bluuebunny/crossref_metadata_2025 huggingface dataset:
Spiro[5.7]trideca‐1,4‐dien‐3‐one
Authors: Kane Vinayak V. , Jones Maitland
Published: November 2003

Spiro[5.7]trideca‐1,4‐dien‐3‐one

intermediate: 1‐(cyclooctylidenemethyl)piperidine

reactant: methyl vinyl ketone (6.44 g, 0.092 mol)

intermediate: spiro[5.7]tridec‐1‐en‐3‐one

product: spiro[5.7]trideca‐1,4‐dien‐3‐one
Preparation and
D
iels–
A
lder Reaction of a Highly Nucleophilic Diene:
trans
‐1‐Methoxy‐3‐Trimethylsiloxy‐1,3‐Butadiene and 5β‐Methoxycyclohexan‐1‐One‐3β,4β‐Dicarboxylic Acid Anhydride
Authors: Danishefsky Samuel , Kitahara Takeshi , Schuda Paul F.
Published: November 2003

Preparation and Diels–Alder reaction of a highly nucleophilic diene:
trans
‐1‐methoxy‐3‐trimethylsiloxy‐1,3‐butadiene and 5β‐methoxycyclohexan‐1‐one‐3β,4β‐dicarboxylic acid anhydride

product:
trans
‐1‐methoxy‐3‐trimethylsiloxy‐1,3‐butadiene

product:
5β‐Methoxycyclohexan‐1‐one‐3β,4β‐dicarboxylic acid anhydride

byproduct: triethylamine hydrochloride
The
C
‐Arylation of β‐Dicarbonyl Compounds: Ethyl 1‐(
p
‐Methoxyphenyl)‐2‐Oxocyclohexanecarboxylate
Authors: Kozyrod Robert P. , Pinhey John T.
Published: November 2003

The
C
‐arylation of β‐dicarbonyl compounds: Ethyl 1‐(
p
‐methoxyphenyl)‐2‐oxocyclohexanecarboxylate

solvent: 1.5 L of hexane

intermediate:
p
‐methoxyphenyllead triacetate

product: ethyl 1‐(
p
‐methoxyphenyl)‐2‐oxocyclohexanecarboxylate
α‐
tert
‐Alkylation of Ketones: 2‐
tert
‐Pentylcyclopentanone
Authors: Reetz M. T. , Chatziiosifidis I. , Hübner F. , Heimbach H.
Published: November 2003

α‐
tert
‐alkylation of ketones: 2‐
tert
‐pentylcyclopentanone

intermediate: 1‐trimethylsiloxycyclopentene

reactant: 11.7 g (0.11 mol) of 2‐chloro‐2‐methylbutane

product: 2‐
tert
‐pentylcyclopentanone
3‐(1‐Hydroxybutyl)‐1‐methylpyrrole and 3‐Butyroyl‐1‐methylpyrrole
Authors: Gilow H. M. , Jones G.
Published: November 2003

3‐(1‐Hydroxybutyl)‐1‐methylpyrrole and 3‐butyroyl‐1‐methylpyrrole

product: 3‐(1‐Hydroxybutyl)‐1‐methylpyrrole (1)

reactant: 60 mL (55 g, 0.676 mol) of 1‐methylpyrrole

reactant: 65 mL (54 g, 0.936 mol) of butyraldehyde

product: 3‐Butyroyl‐1‐methylpyrrole (2)

product: 3‐acetyl‐1‐methylpyrrole
Photocyclization of an Enone to an Alkene: 6‐Methylbicyclo[4.2.0]Octan‐2‐One
Authors: Cargill R. L. , Dalton J. R. , Morton G. H. , Caldwell W. E.
Published: November 2003

Photocyclization of an enone to an alkene: 6‐methylbicyclo[4.2.0]octan‐2‐one

product: 6‐methylbicyclo[4.2.0]octan‐2‐one
Copper(
I
)‐Catalyzed Photocycloaddition: 3,3‐Dimethyl‐
cis
‐bicyclo[3.2.0]heptan‐2‐one
Authors: Salomon Robert G. , Ghosh Subrata
Published: November 2003

Copper(I)‐catalyzed photocycloaddition: 3,3‐Dimethyl‐
cis
‐bicyclo[3.2.0]heptan‐2‐one

intermediate: 2,2‐dimethyl‐4‐pentenal

intermediate: 4,4‐dimethyl‐1,6‐heptadien‐3‐ol

intermediate: 3,3‐dimethyl‐
cis
‐bicyclo[3.2.0]heptan‐2‐ol

product: 3,3‐dimethyl‐
cis
‐bicyclo[3.2.0]heptan‐2‐one

intermediate: 3,3‐dimethyl‐
endo
‐
cis
‐bicyclo[3.2.0]heptan‐2‐ol

intermediate: 3,3‐dimethyl‐
exo
‐
cis
‐bicyclo[3.2.0]heptan‐2‐ol
Reduction of Quinones with Hydriodic Acid: Benz[a]anthracene
Authors: Konieczny Maria , Harvey Ronald G.
Published: November 2003

Reduction of Quinones with Hydriodic Acid: Benz[a]anthracene

product: benz[a]anthracene
Thiete 1,1‐dioxide and 3‐Chlorothiete 1,1‐dioxide
Authors: Sedergran Thomas C. , Dittmer Donald C.
Published: November 2003

Thiete 1,1‐dioxide and 3‐chlorothiete 1,1‐dioxide

intermediate: Thietane 1,1‐dioxide (14.0 g, 0.132 mol)

intermediate: 3‐chlorothietane 1,1‐dioxide (8.0 g, 0.057 mol)

intermediate: 3,3‐dichlorothietane 1,1‐dioxide (4.0 g, 0.023 mol)

product: thiete 1,1‐dioxide

product: 3‐Chlorothiete 1,1‐dioxide
Yeast Reduction of Ethyl Acetoacetate: (
S
)‐( + )‐Ethyl 3‐Hydroxybutanoate
Authors: Seebach Dieter , Sutter Marius A. , Weber Roland H. , Züger Max F.
Published: November 2003

Yeast reduction of ethyl acetoacetate: (
S
)‐( + )‐ethyl 3‐hydroxybutanoate

reactant: 20.0 g (0.154 mol) of ethyl acetoacetate

product: (S)‐( + )‐ethyl 3‐hydroxybutanoate

reactant: ethyl (S)‐( + )‐3‐(3′,5′‐dinitrobenzoyloxy)butanoate

product: methyl 3‐hydroxybutanoate

byproduct: (R‐)‐( − )‐Ethyl 3‐hydroxybutanoate
Asymmetric Hydroboration of 5‐Substituted Cyclopentadienes: Synthesis of Methyl (1
R
,5
R
)‐5‐Hydroxy‐2‐Cyclopentene‐1‐Acetate
Authors: Partridge John J. , Chadha Naresh K. , Uskokovic Milan R.
Published: November 2003

Asymmetric hydroboration of 5‐substituted cyclopentadienes: synthesis of methyl (1
R
,5
R
)‐5‐hydroxy‐2‐cyclopentene‐1‐acetate

intermediate: Cyclopentadiene

reactant: (−)‐α‐pinene

product: methyl (1R,5R)‐5‐hydroxy‐2‐cyclopentene‐1‐acetate

reactant: ( + )‐α‐pinene

product: methyl (1S,5S)‐5‐hydroxy‐2‐cyclopentene‐1‐acetate

unknown: R = CH
3

unknown: R = CH
2
CO
2
CH
3

unknown: R = CH
2
CO
2
‐t‐Bu
(2
SR
,3
SR
)‐2,4‐Dimethyl‐3‐hydroxypentanoic Acid
Authors: Montgomery Stephen H. , Pirrung Michael C. , Heathcock Clayton H.
Published: November 2003

(2
SR
,3
SR
)‐2,4‐Dimethyl‐3‐hydroxypentanoic acid

intermediate: 2,6‐dimethylphenyl propanoate

intermediate: 2′,6′‐Dimethylphenyl (2
SR
,3
SR
)‐2,4‐dimethyl‐3‐hydroxypentanoate.

product: (2
SR
,3
SR
)‐2,4‐dimethyl‐3‐hydroxypentanoic acid
Ricinelaidic Acid Lactone
Authors: Thalmann Adolf , Oertle Konrad , Gerlach Hans
Published: November 2003

Ricinelaidic acid lactone

intermediate: ricinelaidic acid

reactant: 308 mg (1.4 mmol) of 2,2′‐dipyridyl disulfide

product: ricinelaidic acid lactone
Methyl Phenylacetylacetate from Phenylacetyl Chloride and Meldrum's Acid
Authors: Oikawa Y. , Yoshioka T. , Sugano K. , Yonemitsu Osamu
Published: November 2003

Methyl phenylacetylacetate from phenylacetyl chloride and Meldrum's acid

reactant: 25.0 g (0.16 mol) of freshly distilled phenylacetyl chloride

intermediate: acyl Meldrum's acid

product: methyl phenylacetylacetate
One‐Step Homologation of Acetylenes to Allenes: 4‐Hydroxynona‐1,2‐diene
Authors: Crabbé Pierre , Nassim Bahman , Robert‐Lopes Maria‐Teresa
Published: November 2003

One‐Step Homologation of Acetylenes to Allenes: 4‐Hydroxynona‐1,2‐diene

product: 4‐hydroxynona‐1,2‐diene
Deoxygenation of Secondary Alcohols: 3‐Deoxy‐1,2:5,6‐Di‐
O
‐Isopropylidene‐α‐
D
‐
ribo
‐Hexofuranose
Authors: Iacono S. , Rasmussen James R.
Published: November 2003

Deoxygenation of secondary alcohols: 3‐deoxy‐1,2:5,6‐di‐
O
‐isopropylidene‐α‐D‐
ribo
‐hexofuranose

intermediate: 19.25 g (0.055 mol) of 1,2:5,6‐di‐
O
‐isopropylidene‐3‐
O
‐(
S
‐methyldithiocarbonate)‐α‐
D
‐glucofuranose

product: 3‐Deoxy‐1,2:5,6‐di‐
O
‐isopropylidene‐α‐
D
‐
ribo
‐hexofuranose
Diethyl [(2‐Tetrahydropyranyloxy)Methyl]Phosphonate
Authors: Kluge Arthur F.
Published: November 2003

Diethyl [(2‐tetrahydropyranyloxy)methyl]phosphonate

intermediate: 33.63 g (0.2 mol) of diethyl hydroxymethylphosphonate

product: Diethyl [(2‐tetrahydropyranyloxy)methyl]phosphonate
Ethyl isocrotonate
Authors: Taschner Michael J. , Rosen Terry , Heathcock Clayton H.
Published: November 2003

Ethyl isocrotonate

intermediate: ethyl tetrolate

product: ethyl isocrotonate
α‐Hydroxy Ketones from the Oxidation of Enol Silyl Ethers with
m
‐Chloroperbenzoic Acid: 6‐Hydroxy‐ 3,5,5‐Trimethyl‐2‐Cyclohexen‐1‐one
Authors: Rubottom George M. , Gruber John M. , Juve Henrik D. , Charleson Dan A.
Published: November 2003

α‐Hydroxy ketones from the oxidation of enol silyl ethers with
m
‐chloroperbenzoic acid: 6‐hydroxy‐ 3,5,5‐trimethyl‐2‐cyclohexen‐1‐one

solvent: 11.25 mL (80.4 mmol) of freshly distilled diisopropylamine

reactant: 10.0 g (72.4 mmol) of freshly distilled isophorone

reactant: 17.5 mL (137.6 mmol) of freshly distilled chlorotrimethylsilane (TMSCL)

intermediate: 4,6,6‐trimethyl‐2‐trimethylsiloxycyclohexa‐1,3‐diene

solvent: 3–5 mL of petroleum ether

product: 6‐hydroxy‐3,5,5‐trimethyl‐2‐cyclohexen‐1‐one
Phenyl Vinyl Sulfone and Sulfoxide
Authors: Paquette Leo A. , Carr Richard V. C.
Published: November 2003

Phenyl vinyl sulfone and sulfoxide

intermediate: phenyl vinyl sulfide

product: phenyl vinyl sulfone

product: phenyl vinyl sulfoxide
Ring Expansion and Cleavage of Succinoin Derivatives: Spiro[4.5]Decane‐1,4‐dione and Ethyl 4‐Cyclohexyl‐4‐Oxobutanoate
Authors: Nakamura Eiichi , Kuwajima Isao
Published: November 2003

Ring expansion and cleavage of succinoin derivatives: spiro[4.5]decane‐1,4‐dione and ethyl 4‐cyclohexyl‐4‐oxobutanoate

reactant: cyclohexanone diethyl ketal (6.88 g, 40 mmol)

product: spiro[4.5]decane‐1,4‐dione

product: Ethyl 4‐cyclohexyl‐4‐oxobutanoate (4)

reactant: 1,2‐Bis(trimethylsiloxy)cyclobut‐1‐ene

intermediate: 2‐(1‐ethoxycyclohexyl)‐2‐(trimethylsiloxy)cyclobutanone

intermediate: silyl ether 3
4‐Nitroindole
Authors: Bergman Jan , Sand Peter
Published: November 2003

4‐Nitroindole

intermediate: 20.8 g (0.10 mol) of ethyl N‐(2‐methyl‐3‐nitrophenyl)formimidate in 75 mL of dry dimethyl sulfoxide

product: 4‐nitroindole
Allylcarbamates by the Aza‐ene Reaction: Methyl
N
‐(2‐Methyl‐2‐Butenyl)Carbamate
Authors: Kresze Günter , Braxmeier Hans , Münsterer Heribert
Published: November 2003

Allylcarbamates by the aza‐ene reaction: methyl
N
‐(2‐methyl‐2‐butenyl)carbamate

intermediate: Methyl N,N‐dichlorocarbamate.

intermediate: N,N‐Bis(methoxycarbonyl)sulfur diimide.

product: Methyl N‐(2‐methyl‐2‐butenyl)carbamate.
Asymmetric Syntheses Using the
SAMP
‐/
RAMP
‐Hydrazone Method: (
S
)‐(+)‐4‐Methyl‐3‐Heptanone
Authors: Enders Dieter , Kipphardt Helmut , Fey Peter
Published: November 2003

Asymmetric syntheses using the SAMP‐/RAMP‐hydrazone method: (
S
)‐(+)‐4‐methyl‐3‐heptanone

intermediate: SAMP‐hydrazone (S)‐2

intermediate: (S)‐(+)‐4‐Methyl‐3‐heptanone SAMP hydrazone [(ZSS)‐3]

product: (S)‐(+)‐4‐Methyl‐3‐heptanone [(S)‐4]

byproduct: nitrosamine (S)‐5
1‐Deoxy‐2,3,4,6‐Tetra‐
O
‐Acetyl‐1‐(2‐Cyanoethyl)‐α‐
D
‐Glucopyranose
Authors: Giese Bernd , Dupuis J. , Nix Marianne
Published: November 2003

1‐Deoxy‐2,3,4,6‐tetra‐
O
‐acetyl‐1‐(2‐cyanoethyl)‐α‐
D
‐glucopyranose

product: 1‐deoxy‐2,3,4,6‐tetra‐
O
‐acetyl‐1‐(2‐cyanoethyl)‐α‐
D
‐glucopyranose

byproduct: tetra‐
O
‐acetyl‐1,5‐anhydroglucitol

byproduct: 1‐deoxy‐2,3,4,6‐tetra‐
O
‐acetyl‐1‐(2‐cyanoethyl)‐β‐
D
‐glucopyranose
6‐Bromo‐6‐deoxy Hexose Derivatives by Ring Opening of Benzylidene Acetals with
N
‐Bromosuccinimide: Methyl 4‐
O
‐Benzoyl‐6‐bromo‐6‐deoxy‐α‐D‐Glucopyranoside
Authors: Hanessian S.
Published: November 2003

6‐Bromo‐6‐deoxy hexose derivatives by ring opening of benzylidene acetals with
N
‐bromosuccinimide: methyl 4‐
O
‐benzoyl‐6‐bromo‐6‐deoxy‐α‐D‐glucopyranoside

product: Methyl 4‐O‐benzoyl‐6‐bromo‐6‐deoxy‐α‐D‐glucopyranoside

reactant: 20.5 g (72.61 mmol) of methyl 4,6‐O‐benzylidene‐α‐D‐glucopyranoside
Ethyl (
E,Z
)‐2,4‐Decadienoate
Authors: Tsuboi S. , Masuda T. , Mimura S. , Takeda A.
Published: November 2003

Ethyl (
E,Z
)‐2,4‐decadienoate

intermediate: Ethyl 3,4‐decadienoate (1)

product: Ethyl (E,Z)‐2,4‐decadienoate (2)
tert
‐Butyl Acetothioacetate and Its Use in Synthesis: 3‐Acetyl‐4‐hydroxy‐5,5‐dimethylfuran‐2(4
H
)‐one
Authors: Fox Christina M. J. , Ley Steven V.
Published: November 2003

tert
‐Butyl acetothioacetate and its use in synthesis: 3‐Acetyl‐4‐hydroxy‐5,5‐dimethylfuran‐2(4
H
)‐one

intermediate:
S
‐
tert
‐butyl 3‐oxobutanthioate

intermediate: 1‐Carbomethoxy‐1‐methylethyl 3‐oxobutanoate.

product: 3‐Acetyl‐4‐hydroxy‐5,5‐dimethylfuran‐2(5H)‐one.
(±)‐
trans
‐2‐(Phenylsulfonyl)‐3‐phenyloxaziridine
Authors: Vishwakarma Lal C. , Stringer Orum D. , Davis Franklin A.
Published: November 2003

(±)‐
trans
‐2‐(phenylsulfonyl)‐3‐phenyloxaziridine

intermediate: N‐Benzylidenebenzenesulfonamide.

product: (±)‐trans‐2‐(Phenylsulfonyl)‐3‐phenyloxaziridine.

product: R = Ph, Ar = 3NO2Ph

product: R = Ph, Ar = 4NO2Ph

product: R = Me, Ar = Ph

product: R = PhCH2, Ar = Ph
Ethyl α‐(Hydroxymethyl)Acrylate
Authors: Villieras J. , Rambaud M
Published: November 2003

Ethyl α‐(hydroxymethyl)acrylate

product: ethyl α‐(hydroxymethyl) acrylate

product: ethyl α‐(bromomethyl)acrylate
Enantiomeric (S)‐(+)‐ and (R)‐(−)‐1,1′‐Binaphthyl‐2,2′‐Diyl Hydrogen Phosphate
Authors: Jacques J. , Fouquey C.
Published: November 2003

Enantiomeric (S)‐(+)‐ and (R)‐(−)‐1,1′‐binaphthyl‐2,2′‐diyl hydrogen phosphate

intermediate: (±)‐binaphthylphosphoric acid

intermediate: (S)‐(+)‐ and (R)‐(−)‐BNP acid

intermediate: (S)‐(+)‐BNP acid

product: (−)‐BNP acid

reactant: (+)‐cinchonine (Aldrich Chemical Company, Inc.)
(
R
)‐(+)‐1,1′‐Binaphthalene‐2,2′‐diol
Authors: Truesdale Larry K.
Published: November 2003

(
R
)‐(+)‐1,1′‐binaphthalene‐2,2′‐diol

intermediate: (R)‐(−)‐Methyl 1,1′‐binaphthyl‐2,2′‐diylphosphate.

reactant: 20.0 g (57.4 mmol) of (R)‐(−)‐1,1′‐binaphthyl‐2,2′‐diyl hydrogen phosphate

product: (R)‐(+)‐1,1′‐binaphthalene‐2,2′‐diol
(
S
)‐
N,N
‐Dimethyl‐
N
′‐(1‐
tert
‐Butoxy‐3‐Methyl‐2‐Butyl)Formamidine
Authors: Dickman Daniel A. , Boes Michael , Meyers Albert I.
Published: November 2003

(
S
)‐
N,N
‐dimethyl‐
N
′‐(1‐
tert
‐butoxy‐3‐methyl‐2‐butyl)formamidine

intermediate: N‐formyl‐O‐tert‐butylvalinol (1)

product: (S)‐N,N‐dimethyl‐N′‐(1‐tert‐butoxy‐3‐methyl‐2‐butyl)formamidine
Allyltributyltin
Authors: Halligan Noreen G. , Blaszczak Larry C.
Published: November 2003

Allyltributyltin

product: allyltributyltin
2‐(Phenylsulfonyl)‐1,3‐cyclohexadiene
Authors: Bäckvall Jan‐E. , Juntunen Seppo K. , Andell Ove S.
Published: November 2003

2‐(Phenylsulfonyl)‐1,3‐cyclohexadiene

intermediate: trans‐3‐(phenylsulfonyl)‐4‐(chloromercuri)cyclohexene

product: 2‐(phenylsulfonyl)‐1,3‐cyclohexadiene
Domino
D
iels–
A
lder Reaction: 3,3a,3b,4,6a,7a‐Hexahydro‐3,4,7‐metheno‐7
H
‐cyclopenta[
a
]pentalene‐7,8‐dicarboxylic Acid
Authors: Taylor Richard T. , Pelter Michael W. , Paquette Leo A.
Published: November 2003

Domino Diels–Alder Reaction: 3,3a,3b,4,6a,7a‐hexahydro‐3,4,7‐metheno‐7
H
‐cyclopenta[
a
]pentalene‐7,8‐dicarboxylic acid

product: 3,3a,3b,4,6a,7a‐Hexahydro‐3,4,7‐metheno‐7H‐cyclopenta[a]pentalene‐7,8‐dicarboxylic acid
4,13‐Diaza‐18‐Crown‐6
Authors: Gatto Vincent J. , Miller Steven R. , Gokel George W.
Published: November 2003

4,13‐Diaza‐18‐crown‐6

intermediate: 1,10‐dibenzyl‐4,7‐dioxa‐1,10‐diazadecane

reactant: 1,2‐bis(2‐iodoethoxy)ethane (39.3 g, 106 mmol)

intermediate:
N,N
′‐dibenzyl‐4,13‐diaza‐18‐crown‐6

product: 4,13‐diaza‐18‐crown‐6
Enantiomerically Pure Ethyl (
R
)‐ and (
S
)‐ 2‐Fluorohexanoate by Enzyme‐Catalyzed Kinetic Resolution
Authors: Kalaritis P. , Regenye R. W.
Published: November 2003

Enantiomerically pure ethyl (
R
)‐ and (
S
)‐ 2‐fluorohexanoate by enzyme‐catalyzed kinetic resolution

product: ethyl 2‐fluorohexanoate

product: ethyl (R)‐2‐fluorohexanoate

intermediate: (S)‐2‐fluorohexanoic acid

product: 28.4 g (0.175 mol) of ethyl (S)‐2‐fluorohexanoate (81% ee)
Hydromagnesiation reaction of propargylic alcohols: (
E
)‐3‐pentyl‐2‐nonene‐1,4‐diol from 2‐octyn‐1‐ol
Authors: Sato Fumie , Kobayashi Yuichi
Published: November 2003

Hydromagnesiation reaction of propargylic alcohols: (
E
)‐3‐pentyl‐2‐nonene‐1,4‐diol from 2‐octyn‐1‐ol

product: (E)‐3‐Pentyl‐2‐nonene‐1,4‐diol (4).

byproduct: (Z)‐2‐octen‐1‐ol (3)

byproduct: (Z)‐3‐methyl‐2‐octen‐1‐ol (5)
Direct NucleophilicAcylation by the Low‐Temperature, In Situ Generation of Acyllithium Reagents; α‐Hydroxy Ketones from Ketones: 3‐Hydroxy‐2,2,3‐trimethyloctan‐4‐one from Pinacolone
Authors: Hui Richard , Seyferth Dietmar
Published: November 2003

Direct nucleophilic acylation by the low‐temperature, in situ generation of acyllithium reagents; α‐hydroxy ketones from ketones: 3‐hydroxy‐2,2,3‐trimethyloctan‐4‐one from pinacolone

product: 3‐hydroxy‐2,2,3‐trimethyloctan‐4‐one
A General Method for the Preparation of 9‐, 10‐, and 11‐Membered Unsaturated Macrolides: Synthesis of 8‐Propionyl‐(
E
)‐5‐Nonenolide
Authors: Webb Kevin S. , Asirvatham Edward , Posner Gary H.
Published: November 2003

A general method for the preparation of 9‐, 10‐, and 11‐membered unsaturated macrolides: synthesis of 8‐propionyl‐(
E
)‐5‐nonenolide

product: 8‐propionyl‐(E)‐5‐nonenolide
A Stable Chiral 1,4‐Dihydropyridine Equivalent for the Asymmetric Synthesis of Substituted Piperidines: 2‐Cyano‐6‐Phenyloxazolopiperidine
Authors: Bonin Martine , Grierson David S. , Royer Jacques , Husson Henri‐Philippe
Published: November 2003

A Stable chiral 1,4‐dihydropyridine equivalent for the asymmetric synthesis of substituted piperidines: 2‐cyano‐6‐phenyloxazolopiperidine

reactant: 10 g (0.073 mol) of (−)‐phenylglycinol

product: 2‐cyano‐6‐phenyloxazolopiperidine
(E)‐1‐Benzyl‐3‐(1‐Iodoethylidene)Piperidine: Nucleophile‐Promoted Alkyne‐Iminium Ion Cyclizations
Authors: Arnold H. , Overman L. E. , Sharp M. J. , Witschel M. C.
Published: November 2003

(E)‐1‐benzyl‐3‐(1‐iodoethylidene)piperidine: nucleophile‐promoted alkyne‐iminium ion cyclizations

reactant: 5.0 g (51 mmol) of 4‐hexyn‐1‐ol

intermediate: 4‐hexyn‐1‐yl methanesulfonate

intermediate: N‐Benzyl‐4‐hexyn‐1‐amine

product: (E)‐1‐Benzyl‐3‐(1‐iodoethylidene)piperidine
Asymmetric Hydrogenation of 3‐Oxo Carboxylates Using Binap‐Ruthenium Complexes: (R)‐(−)‐Methyl3‐Hydroxybutanoate
Authors: Kitamura Masato , Tokunaga Makoto , Ohkuma Takeshi , Noyori Ryoji
Published: November 2003

Asymmetric hydrogenation of 3‐oxo carboxylates using binap‐ruthenium complexes: (R)‐(−)‐methyl 3‐hydroxybutanoate

catalyst: [(R)‐2,2′‐Bis(diphenylphosphino)‐1,1′‐binaphthyl]ruthenium(II) complex

product: (R)‐(−)‐methyl 3‐hydroxybutanoate
2‐Methylene‐1,3‐Dithiolane
Authors: Dahnke Karl R. , Paquette Leo A.
Published: November 2003

2‐Methylene‐1,3‐dithiolane

intermediate: 2‐chloromethyl‐1,3‐dithiolane

product: 2‐methylene‐1,3‐dithiolane
DiastereoselectiveHomologation of
D
‐(R)‐Glyceraldehyde Acetonide using 2‐(Trimethylsilyl)Thiazole: 2‐O‐Benzyl‐3,4‐Isopropylidene‐
D
‐Erythrose
Authors: Dondoni Alessandro , Merino Pedro
Published: November 2003

Diastereoselective homologation of
D
‐(R)‐glyceraldehyde acetonide using 2‐(trimethylsilyl)thiazole: 2‐O‐benzyl‐3,4‐isopropylidene‐
D
‐erythrose

intermediate: 2‐(trimethylsilyl)thiazole

intermediate: (1R)‐2,3‐Di‐O‐isopropylidene‐1‐(2‐thiazolyl)‐D‐glycitol

intermediate: (1R)‐O‐Benzyl‐2,3‐di‐O‐isopropylidene‐1‐(2‐thiazolyl)‐D‐glycitol

product: 2‐O‐benzyl‐3,4‐isopropylidene‐D‐erythrose
(2S,4S)‐2,4,5‐Trihydroxypentanoic acid 4,5‐Acetonide Methyl Ester
Authors: Sun Ruen Chu , Okabe Masami
Published: November 2003

(2S,4S)‐2,4,5‐trihydroxypentanoic acid 4,5‐acetonide methyl ester

intermediate: Tri‐O‐acetyl‐D‐xylono‐1,4‐lactone

intermediate: Di‐O‐acetyl‐3‐deoxy‐D‐arabino‐1,4‐lactone

product: (2S,4S)‐2,4,5‐Trihydroxypentanoic acid 4,5‐acetonide methyl ester
Preparation and Reactions of Alkenylchromium Reagents: 2‐Hexyl‐5‐Phenyl‐1‐Penten‐3‐ol
Authors: Takai Kazuhiko , Sakogawa Koichi , Kataoka Yasutaka , Oshima Koichiro , Utimoto Kiitiro
Published: November 2003

Preparation and reactions of alkenylchromium reagents: 2‐hexyl‐5‐phenyl‐1‐penten‐3‐ol

reactant: 1‐octyne (11 g, 0.10 mol, ) and dry hexane (100 mL, )

reactant: trifluoromethanesulfonic acid (TfOH, 4.9 mL, 55 mmol, )

intermediate: 1‐hexylethenyl triflate

solvent: oxygen‐free N,N‐dimethylformamide (DMF, 250 mL, )

reactant: 3‐phenylpropanal (2.7 g, 20 mmol, ) in DMF (20 mL)

product: 2‐hexyl‐5‐phenyl‐1‐penten‐3‐ol
Stereoselective Alkene Synthesis via 1‐Chloro‐1‐[(Dimethyl)Phenylsilyl]Alkanes and α‐(Dimethyl)Phenylsilyl Ketones: 6‐Methyl‐6‐Dodecene
Authors: Barrett Anthony G. M. , Flygare John A. , Hill Jason M. , Wallace Eli M.
Published: November 2003

Stereoselective alkene synthesis via 1‐chloro‐1‐[(dimethyl)phenylsilyl]alkanes and α‐(dimethyl)phenylsilyl ketones: 6‐methyl‐6‐dodecene

reactant: 16.78 g (20.0 mL, 167.5 mmol) of hexanal

intermediate: 1‐[(dimethyl)phenylsilyl]‐1‐hexanol

product: 1‐chloro‐1‐[(dimethyl)phenylsilyl]hexane

product: (Z)‐6‐methyl‐6‐dodecene

product: (E)‐6‐methyl‐6‐dodecene
4‐Dodecylbenzenesulfonyl Azides
Authors: Hazen G. G. , Bollinger F. W. , Roberts F. E. , Russ W. K. , Seman J. J. , Staskiewicz S.
Published: November 2003

4‐dodecylbenzenesulfonyl azides

product: dodecylbenzenesulfonyl azides
1,3,5‐Cyclooctatriene
Authors: Oda Masaji , Kawase Takeshi , Kurata Hiroyuki
Published: November 2003

1,3,5‐Cyclooctatriene

reactant: 216.4 g (2.0 mol) of 1,5‐cyclooctadiene

intermediate: 3‐bromo‐1,5‐cyclooctadiene and 6‐bromo‐1,4‐cyclooctadiene

product: 1,3,5‐cyclooctatriene
(R)‐(−)‐2,2‐Diphenylcyclopentanol
Authors: Denmark Scott E. , Marcin Lawrence R. , Schnute Mark E. , Thorarensen Atli
Published: November 2003

(R)‐(−)‐2,2‐diphenylcyclopentanol

intermediate: 2‐Amino‐3,3‐diphenyl‐1‐cyclopentene‐1‐carbonitrile

reactant: 28.3 mL (0.29 mol) of 4‐bromobutyronitrile

intermediate: 2,2‐Diphenylcyclopentanone

product: (R)‐(−)‐2,2‐diphenylcyclopentanol

catalyst: 1.5 g (93% recovery) of (S)‐α,α‐diphenyl‐2‐pyrrolidinemethanol

solvent: hexane

reactant: 4‐Iodobutyronitrile
[3+2]‐Anionic Electrocyclization Using 2,3‐Bis(Phenylsulfonyl)‐1,3‐Butadiene: trans‐4,7,7‐Tricarbomethoxy‐2‐Phenylsulfonylbicyclo[3.3.0]Oct‐1‐Ene
Authors: Padwa Albert , Watterson Scott H. , Ni Zhijie
Published: November 2003

[3+2]‐Anionic electrocyclization using 2,3‐bis(phenylsulfonyl)‐1,3‐butadiene: trans‐4,7,7‐Tricarbomethoxy‐2‐phenylsulfonylbicyclo[3.3.0]oct‐1‐ene

intermediate: 2,3‐bis(phenylsulfinyl)‐1,3‐butadiene

reactant: 2,3‐bis(phenylsulfonyl)‐1,3‐butadiene

intermediate: dimethyl (E)‐5‐methoxycarbonyl‐2‐hexenedioate

product: trans‐4,7,7‐tricarbomethoxy‐2‐phenylsulfonylbicyclo[3.3.0]oct‐1‐ene
Preparation of Bicyclo[3.2.0]Hept‐3‐en‐6‐ones: 1,4‐Dimethylbicyclo[3.2.0]Hept‐3‐en‐6‐one
Authors: Rosini Goffredo , Confalonieri Giovanni , Marotta Emanuela , Rama Franco , Righi Paolo
Published: November 2003

Preparation of bicyclo[3.2.0]hept‐3‐en‐6‐ones: 1,4‐dimethylbicyclo[3.2.0]hept‐3‐en‐6‐one

intermediate: Methyl 3,6‐dimethyl‐3‐hydroxy‐6‐heptenoate

intermediate: 3,6‐dimethyl‐3‐hydroxy‐6‐heptenoic acid

product: 1,4‐dimethylbicyclo[3.2.0]hept‐3‐en‐6‐one
A Simple and Convenient Method for the Preparation of (Z)‐β‐Iodoacrolein and of (Z)‐ or (E)‐γ‐Iodo Allylic Alcohols: (Z)‐ and (E)‐1‐Iodohept‐1‐en‐3‐ol
Authors: Marek Ilane , Meyer Christophe , Normant Jean‐F.
Published: November 2003

A simple and convenient method for the preparation of (Z)‐β‐iodoacrolein and of (Z)‐ or (E)‐γ‐iodo allylic alcohols: (Z)‐ and (E)‐1‐iodohept‐1‐en‐3‐ol

intermediate: Ethyl (Z)‐β‐iodoacrylate

product: (Z)‐1‐Iodohept‐1‐en‐3‐ol

product: (E)‐1‐Iodohept‐1‐en‐3‐ol

product: (Z)‐β‐Iodoacrolein, 4
Allylic Alcohols by Alkene Transfer from Zirconium to Zinc: 1‐[(tert‐Butyldiphenylsilyl)oxy]‐Dec‐3‐en‐5‐ol
Authors: Wipf Peter , Xu Wenjing
Published: November 2003

Allylic alcohols by alkene transfer from zirconium to zinc: 1‐[(tert‐butyldiphenylsilyl)oxy]‐dec‐3‐en‐5‐ol

intermediate: tert‐butyl(but‐3‐ynyloxy)diphenylsilane

product: 1‐[(tert‐butyldiphenyl‐silyl)oxy]‐dec‐3‐en‐5‐ol
Asymmetric Synthesis of Diethyl (R)‐(−)‐(1‐Amino‐3‐Methylbutyl)Phosphonate
Authors: Smith Amos B. , Yager Kraig M. , Phillips Barton W. , Taylor Carol M.
Published: November 2003

Asymmetric synthesis of diethyl (R)‐(−)‐(1‐amino‐3‐methylbutyl)phosphonate

intermediate: (R)‐(−)‐1‐Amino‐1‐phenyl‐2‐methoxyethane (2)

intermediate: Diethyl (R)‐(−)‐[1‐((N‐(R)‐(1‐phenyl‐2‐methoxyethyl)amino)‐3‐methylbutyl)]phosphonate (4)

product: Diethyl (R)‐(−)‐(1‐amino‐3‐methylbutyl)phosphonate (5)

reactant: diethyl phosphite (29.3 g, 212.1 mmol)

product: (S)‐(+)‐Phosphovaline diethyl ester

product: (S)‐(+)‐phosphoalanine diethyl ester

product: (S)‐(+)‐phosphoserine diethyl ester

product: (R)‐(−)‐Phospholeucine

product: (S)‐(−)‐Phosphomethionine

product: (R)‐(+)‐Phosphomethionine

product: (R)‐(−)‐Phosphoglutamic acid

product: (R)‐(−)‐Phospho(phenylglycine)
Accelerated Suzuki Coupling Via a Ligandless Palladium Catalyst: 4‐Methoxy‐2′‐Methylbiphenyl
Authors: Goodson Felix E. , Wallow Thomas I. , Novak Bruce M.
Published: November 2003

Accelerated suzuki coupling via a ligandless palladium catalyst: 4‐methoxy‐2′‐methylbiphenyl

product: 4‐methoxy‐2′‐methylbiphenyl
2‐(4‐Methoxyphenyl)‐2‐Cyclohexen‐1‐One: Preparation of 2‐Iodo‐2‐Cyclohexen‐1‐One and Suzuki Coupling With 4‐Methoxyphenylboronic Acid
Authors: Ruel Frederic S. , Braun Matthew P. , Johnson Carl R.
Published: November 2003

2‐(4‐Methoxyphenyl)‐2‐cyclohexen‐1‐one: preparation of 2‐iodo‐2‐cyclohexen‐1‐one and suzuki coupling with 4‐methoxyphenylboronic acid

intermediate: 2‐iodo‐2‐cyclohexen‐1‐one

product: 2‐(4‐methoxyphenyl)‐2‐cyclohexen‐1‐one
Efficient Synthesis of Bromides from Carboxylic Acids Containing a Sensitive Functional Group: Dec‐9‐Enyl Bromide from 10‐Undecenoic Acid
Authors: Barton Derek H. R. , MacKinnon John , Perchet Roland N. , Tse Chi‐Lam (Ivan)
Published: November 2003

Efficient synthesis of bromides from carboxylic acids containing a sensitive functional group: dec‐9‐enyl bromide from 10‐undecenoic acid

intermediate: N‐(10‐Undecenoyloxy)pyridine‐2‐thione (3)

product: dec‐9‐enyl bromide

reactant: 10‐Undecenoic acid was purchased from the
Aldrich Chemical Company, Inc
.
4‐Dimethylamino‐N‐Triphenylmethylpyridinium Chloride
Authors: Bhatia Ashok V. , Chaudhary Sunil K. , Hernandez Oscar
Published: November 2003

product: 4‐dimethylamino‐N‐triphenylmethylpyridinium chloride
N‐Vinylpyrrolidin‐2‐One as a 3‐Aminopropyl Carbanion Equivalent in the Synthesis of Substituted 1‐Pyrrolines: 2‐Phenyl‐1‐Pyrroline
Authors: Sorgi Kirk L. , Maryanoff Cynthia A. , McComsey David F. , Maryanoff Bruce E.
Published: November 2003

N‐Vinylpyrrolidin‐2‐One as a 3‐Aminopropyl Carbanion Equivalent in the Synthesis of Substituted 1‐Pyrrolines: 2‐Phenyl‐1‐Pyrroline
(4R,5R)‐2,2‐Dimethyl‐α,α,α′,α′‐Tetra(Naphth‐2‐yl)‐1,3‐Dioxolane‐4,5‐Dimethanol from Dimethyl Tartrate and 2‐Naphthyl‐Magnesium Bromide
Authors: Beck Albert K. , Gysi Peter , Vecchia Luigi La , Seebach Dieter
Published: November 2003

(4R,5R)‐2,2‐dimethyl‐α,α,α′,α′‐tetra(naphth‐2‐yl)‐1,3‐dioxolane‐4,5‐dimethanol from dimethyl tartrate and 2‐naphthyl‐magnesium bromide

product: (4R,5R)‐2,2‐Dimethyl‐α,α,α′,α′‐tetra(naphth‐2‐yl)‐1,3‐dioxolane‐4,5‐dimethanol

intermediate: (R,R)‐dimethyl O,O‐isopropylidenetartrate (48.1 g, 0.22 mol)
(R,R)‐ and (S,S)‐N,N′‐Dimethyl‐1,2‐Diphenylethylene‐1,2‐Diamine
Authors: Alexakis Alex , Aujard Isabelle , Kanger Tonis , Mangeney Pierre
Published: November 2003

(R,R)‐ and (S,S)‐N,N′‐dimethyl‐1,2‐diphenylethylene‐1,2‐diamine

intermediate: N‐Methylbenzimine

intermediate: meso‐ and dl‐N,N′‐Dimethyl‐1,2‐diphenylethylenediamine

intermediate: dl‐N,N′‐Dimethyl‐1,2‐diphenylethylene‐diamine

product: (R,R)‐(+)‐N,N′‐Dimethyl‐1,2‐diphenylethylenediamine

product: (S,S)‐(−)‐N,N′‐Dimethyl‐1,2‐diphenylethylenediamine

byproduct: 2‐5% of N‐methylbenzylamine
Preparation of Enantiomerically Pure α‐N,N‐Dibenzylamino Aldehydes: S‐2‐(N,N‐Dibenzylamino)‐3‐Phenylpropanal
Authors: Reetz Manfred T. , Drewes Mark W. , Schwickardi Renate
Published: November 2003

Preparation of enantiomerically pure α‐N,N‐dibenzylamino aldehydes: S‐2‐(N,N‐dibenzylamino)‐3‐phenylpropanal

intermediate: benzyl (S)‐2‐(N,N‐dibenzylamino)‐3‐phenylpropanoate

product: (S)‐2‐(N,N‐Dibenzylamino)‐3‐phenylpropanal

intermediate: 3.31 g (10 mmol) of (S)‐2‐(N,N‐dibenzylamino)‐3‐phenyl‐1‐propanol in 5 mL of dichloromethane
Conversion of Nitriles into Tertiary Amines: N,N‐Dimethylhomoveratrylamine
Authors: Rousselet Guilhem , Capdevielle Patrice , Maumy Michel
Published: November 2003

Conversion of nitriles into tertiary amines: N,N‐dimethylhomoveratrylamine

intermediate: 2‐(3,4‐Dimethoxyphenyl)‐N,N‐dimethylacetamidine

product: N,N‐dimethylhomoveratrylamine

product: CH
3
CH
2
NH(CH
2
)
5
CH
3

product: CH
3
CH
2
NHCH
2
C
6
H
5
Generation and Use of Lithium Pentafluoropropen‐2‐Olate: 4‐Hydroxy‐1,1,1,3,3‐Pentafluoro‐2‐Hexanone Hydrate
Authors: Qian Cheng‐Ping , Liu Yu‐Zhong , Tomooka Katsuhiko , Nakai Takeshi
Published: November 2003

Generation and use of lithium pentafluoropropen‐2‐olate: 4‐hydroxy‐1,1,1,3,3‐pentafluoro‐2‐hexanone hydrate

intermediate: lithium pentafluoropropen‐2‐olate

product: 4‐hydroxy‐1,1,1,3,3‐pentafluoro‐2‐hexanone hydrate
Bromofluorination of Alkenes: 1‐Bromo‐2‐Fluoro‐2‐Phenylpropane
Authors: Haufe Günter , Alvernhe Gerard , Laurent André , Ernet Thomas , Goj Olav , Kröger Stefan , Sattler Andreas
Published: November 2003

Bromofluorination of alkenes: 1‐bromo‐2‐fluoro‐2‐phenylpropane

product: 1‐Bromo‐2‐fluoro‐2‐phenylpropane
Mono‐C‐Methylation of Arylacetonitriles and Methyl Arylacetates by Dimethyl Carbonate: A General Method for the Synthesis of Pure 2‐Arylpropionic Acids. 2‐Phenylpropionic Acid
Authors: Tundo Pietro , Selva Maurizio , Bomben Andrea
Published: November 2003

Mono‐C‐methylation of arylacetonitriles and methyl arylacetates by dimethyl carbonate: A general method for the synthesis of pure 2‐arylpropionic acids. 2‐phenylpropionic acid

reactant: dimethyl carbonate (DMC)

product: 2‐phenylpropionic acid (3)

intermediate: 2‐phenylpropionitrile (2)
Generation of 1‐Propynyllithium from (Z/E)‐1‐Bromo‐1‐Propene:
Authors: Toussaint Dominique , Suffert Jean
Published: November 2003

Generation of 1‐propynyllithium from (Z/E)‐1‐bromo‐1‐propene:

product: 6‐phenylhex‐2‐yn‐5‐en‐4‐ol

reactant: 1‐Bromo‐1‐propene was purchased from Lancaster Synthesis Inc. (mixture of isomers, technical grade)
2‐Chlorophenyl Phosphorodichloridothioate
Authors: Ravikumar Vasulinga T. , Ross Bruce
Published: November 2003

2‐Chlorophenyl phosphorodichloridothioate

product: 2‐chlorophenyl phosphorodichloridothioate
Preparation of (R,R)‐1,2:4,5‐Diepoxypentane
Authors: Rychnovsky Scott D. , Griesgraber George , Powers Jay P.
Published: November 2003

Preparation of (R,R)‐1,2:4,5‐diepoxypentane

intermediate:
Bis(1,5‐dichloro‐2,4‐pentanedione)copper(II) complex

intermediate:
1,5‐Dichloro‐2,4‐pentanedione

intermediate:
(2R,4R)‐1,5‐dichloro‐2,4‐pentanediol

product:
(R,R)‐1,2:4,5‐diepoxypentane
Sulfinimines (Thiooximine S‐Oxides): Asymmetric Synthesis of Methyl (R)‐(+)‐β‐Phenylalanate from (S)‐(+)‐N‐(Benzylidene)‐p‐Toluenesulfinamide
Authors: Fanelli Dean L. , Szewczyk Joanna M. , Zhang Yulian , Reddy G. Venkat , Burns David M. , Davis Franklin A.
Published: November 2003

Sulfinimines (thiooximine s‐oxides): Asymmetric synthesis of methyl (R)‐(+)‐β‐phenylalanate from (S)‐(+)‐N‐(benzylidene)‐p‐toluenesulfinamide

intermediate: 10.35 g (66.8 mmol) of (S)‐(+)‐p‐toluenesulfinamide
(2)

intermediate: 2.65 g (10.9 mmol) of (S)‐(+)‐N‐(benzylidene)‐
p
‐toluenesulfinamide
(3)
in 50 mL of anhydrous ether

intermediate: 2.13 g (6.7 mmol) of (S
s
,R)‐(+)‐methyl N‐(p‐tolylsulfinyl)‐3‐amino‐3‐phenylpropanoate
(4)

product: methyl (R)‐(+)‐β‐phenylalanate
Ethyl Adipate
Authors: Mićović V. M.
Published: November 2003

Ethyl adipate

product: ethyl adipate
Triphenylcarbinol
Authors: Bachmann W. E. , Hetzner H. P.
Published: November 2003

Triphenylcarbinol

product: triphenylcarbinol
2,4,4‐Trimethylcyclopentanone
Authors: Ryerson George D. , Wasson Richard L. , House Herbert O.
Published: November 2003

2,4,4‐Trimethylcyclopentanone

reactant: 20 ml. (0.16 mole) of boron trifluoride etherate

product: 2,4,4‐trimethylcyclopentanone

byproduct: 2‐formyl‐2,4,4‐trimethylcyclopentanone

byproduct: 3,5,5‐trimethyl‐1,2‐cyclohexanedione
Methyl (
E
)‐3‐Nitroacrylate
Authors: McMurry John E. , Musser John H. , Fleming Ian , Fortunak J. , Nübling C.
Published: November 2003

Methyl (
E
)‐3‐nitroacrylate

solvent: 30% diethyl ether/petroleum ether

intermediate: methyl 2‐iodo‐3‐nitropropionate

product: methyl (
E
)‐3‐nitroacrylate

solvent: 30% ether/petroleum ether
p
‐
tert
‐Butylcalix[6]arene
Authors: Gutsche C. D. , Dhawan B. , Leonis M. , Stewart D.
Published: November 2003

p
‐
tert
‐Butylcalix[6]arene

reactant:
p
‐
tert
‐Butylphenol from Aldrich Chemical Company, Inc.

product:
p
‐
tert
‐Butylcalix[6]arene
Cyclopentadiene Annulation via the
S
kattebøl Rearrangement: (1
R
)‐9,9‐Dimethyltricyclo‐[6.1.1.0
2,6
]Deca‐2,5‐Diene
Authors: Paquette Leo A. , McLaughlin Mark L.
Published: November 2003

Cyclopentadiene annulation via the Skattebøl rearrangement: (1
R
)‐9,9‐dimethyltricyclo‐[6.1.1.0
2,6
]deca‐2,5‐diene

intermediate: Dibromocarbene addition to (1R)‐nopadiene.

reactant: 29.6 g (0.20 mol) of (1R)‐nopadiene

intermediate: 200 g (0.624 mol) of (1R)‐nopyl tosylate and 1000 mL of dimethyl sulfoxide

product: (1R)‐9,9‐Dimethyltricyclo[6.1.1.02,6]deca‐2,5‐diene
Ischaemic preconditioning modulates the activity of Kupffer cells during in vivo reperfusion injury of rat liver
Authors: Cavalieri Barbara , Perrelli Maria‐Giulia , Aragno Manuela , Ramadori Pierluigi , Poli Giuseppe , Cutrìn Juan C.
Published: November 2003

This work was performed to elucidate further the main cellular events underlying the protective effect of ischaemic preconditioning in an in vivo rat liver model of 90 min ischaemia followed by 30 min reperfusion. A significant attenuation of the various aspects of post‐ischaemic injury, namely necrosis and the levels of hydrogen peroxide and 5‐ and 15‐hydroperoxyeicosatetraenoic acids, was afforded by the prior application of a short cycle of ischaemia/reperfusion (10 + 10 min) or when rats were previously treated with gadolinium chloride. However, when preconditioning was applied on Kupffer cell‐depleted livers, no additional level of ischaemic tolerance was obtained. In terms of cellular pathology, this result could be suggestive of Kupffer cells as the target of the preconditioning phenomenon during the warm ischaemia/reperfusion injury. Accordingly, modulation of Kupffer cell activity was associated with a well‐preserved hepatocyte integrity, together with low levels of pro‐oxidant generation during reperfusion. As activated Kupffer cells can generate and release potentially toxic substances, their modulation by ischaemic preconditioning could help to provide new surgical and/or pharmacological strategies to protect the liver against reperfusion damage. Copyright © 2003 John Wiley & Sons, Ltd.
Evidence that macrophages transfer arachidonic acid and cholesterol to tissues in vivo
Authors: Peres C. M. , Homem de Bittencourt P. I. , Mendonça J. R. , Curi R.
Published: November 2003

Our previous studies have shown that [14C]‐labelled cholesterol (CHOL) and arachidonic acid (AA) are transferred from macrophages (Mϕ) to lymphocytes (LY) when these cells are co‐cultured. In this study, we investigated whether these lipids can be transferred from control and thioglycollate‐elicited Mϕ (THIO‐elicited Mϕ) to various tissues and organs in vivo. For this purpose, control and THIO‐elicited Mϕ were pre‐treated with [14C]‐AA and [3H]‐CHOL and then injected into the jugular vein of adult rats. More than 75% of the radioactivity injected was found in the liver of rats treated with [14C]‐AA labelled‐Mϕ either control and THIO‐stimulated. The radioactivity of [3H]‐CHOL labelled Mϕ was transferred mainly to the liver (51% in the control Mϕ and 23% in the thioglycollate Mϕ7) but it was also found in the kidney, lung and spleen. These results support the proposition that the transfer of lipids between cells also occurs in vivo. The full significance of this phenomenon however remains to be elucidated. Copyright © 2003 John Wiley & Sons, Ltd.
Increased insulin‐like growth factor‐I gene expression precedes left ventricular cardiomyocyte hypertrophy in a rapidly‐hypertrophying rat model system
Authors: Huang Chi‐Yang , Buchanan David L. , Gordon Robert L. , Sherman Matthew J. , Razzaq Jamil , White Karen , Buetow Dennis E.
Published: November 2003

Chronic pressure overload leads to an increase in the size, i.e. hypertrophy, of cardiomyocytes in the heart. However, the molecular mechanisms underlying this hypertrophy are not understood. Insulin‐like growth factor‐I (IGF‐I) synthesized locally in the heart is known to be associated with the hypertrophic process. So far, however, cardiac IGF‐I gene expression in the widely used rat model system has only been shown to be increased when the hypertrophy induced by pressure‐overload was already established. Therefore, the question of whether IGF‐I serves as an initiating or early‐enhancing factor for the cardiac hypertrophy remains unanswered. Here, cardiac hypertension and hypertrophy were rapidly induced in the rat by complete constriction of the abdominal aorta between the origins of the renal arteries. Carotid arterial systolic blood pressure remained unchanged in sham rats but increased rapidly in the pressure‐overloaded constricted rats with a sustained hypertension established by 3 days. Hypertrophy of left ventricular (LV) cardiomyocytes in constricted rats also occurred by 3 days. However, this hypertrophy was preceded by increases in LV IGF‐I mRNA and protein which occurred within 1 day. These results support the hypothesis that cardiac‐synthesized IGF‐I is an initiating or early‐enhancing factor for hypertrophy of LV cardiomyocytes. Copyright © 2003 John Wiley & Sons, Ltd.
Effect of melatonin on cholestatic oxidative stress under constant light exposure
Authors: Cruz Adolfo , Padillo Francisco J. , Granados Jose , Túnez Isaac , Muñoz M. Carmen , Briceño Javier , Pera‐Madrazo Carlos , Montilla Pedro
Published: November 2003

This study was designed to evaluate the effect of melatonin on cholestatic oxidative stress under constant light exposure. Cholestasis was induced by double ligature and section of the extra‐hepatic bile duct. Melatonin was injected i.p.(1000 μg kg−1 day−1). Malondialdehyde, reduced glutathione, catalase, superoxide dismutase, glutathione reductase, peroxidase and transferase were determined in liver. After bile‐duct obstruction and under constant light exposure, an increase in malondialdehyde (p < 0.05) and a slight decrease in reduced glutathione were seen. Enzyme activity, with the exception of glutathione reductase, had significantly diminished. After melatonin administration, malondialdehyde fell (p < 0.001), whereas there was an increase in reduced glutathione (p < 0.0001) compared with untreated controls. Constant light exposure was associated with an increase in hepatic oxidative stress. Treatment with melatonin decreased lipid peroxide synthesis, and permitted a recovery of both reduced glutathione and scavenger enzyme activity. Copyright © 2003 John Wiley & Sons, Ltd.
Restenosis due to underexpansion of sirolimus‐eluting stent in a bifurcation lesion
Authors: Takebayashi Hideo , Kobayashi Yoshio , Dangas George , Fujii Kenichi , Mintz Gary S. , Stone Gregg W. , Moses Jeffrey W. , Leon Martin B.
Published: November 2003

Even in the drug‐eluting stent era, percutaneous coronary intervention in bifurcation lesions is complex and technically demanding, and considerable expertise is required. This case report describes in‐stent restenosis due to stent underexpansion after kissing stents using sirolimus‐eluting stents. Catheter Cardiovasc Interv 2003;60:496–499. © 2003 Wiley‐Liss, Inc.
Balloon angioplasty of postoperative coarctation in the transverse arch in infants: Protecting the common carotid artery
Authors: Tomita Hideshi , Yazaki Satoshi , Kimura Kohji , Hayashi George , Fujita Hideki , Okada Yoko , Watanabe Ken , Kurosaki Ken‐ichi , Ono Yasuo , Yagihara Toshikatsu , Echigo Shigeyuki
Published: November 2003

We performed balloon angioplasty in three patients with postoperative coarctation in the transverse arch adjacent to the left common carotid artery. The age at arch reconstruction was 5, 6, and 2 days, while the interval between operation and balloon dilatation was 59 days, 87 days, and 12 months, respectively. Two balloons, one in the stenosis and the other in the left common carotid artery, were introduced over a wire sequentially and inflated simultaneously until the waist of the balloon in the arch disappeared. After balloon dilatation, a significant reduction in the peak‐to‐peak pressure gradient and an increase in vessel diameters were observed in all patients. Further growth of the transverse arch was documented at follow‐up in two patients. No aneurysm has been detected in any patients. We believe that placing a protective balloon in the neck vessel increases safety during balloon dilatation of coarctation in the transverse arch. Catheter Cardiovasc Interv 2003;60:529–533. © 2003 Wiley‐Liss, Inc.
Randomized study to compare balloon angioplasty and elective stent implantation in venous bypass grafts: The Venestent Study
Authors: Hanekamp Clara E.E. , Koolen Jacques J. , den Heijer Peter , Schalij Martin J. , Piek Jan J. , Bär Frits W.H.M. , De Scheerder Iwan , Bonnier Hans J.R.M. , Pijls Nico H.J.
Published: November 2003

The aim of the study was to compare acute and long‐term angiographic and clinical outcome of balloon angioplasty and elective stenting in de novo lesions in the body of a saphenous vein graft (SVG). A total of 150 patients, with de novo lesions in SVG, were randomly assigned to balloon angioplasty or elective Wiktor I stent implantation. The angiographic restenosis rate at 6‐month follow‐up was 32.8% in the balloon group and 19.1% in the stent group (P = 0.069). At 1‐year follow‐up, target vessel revascularization rate was 31.4% vs. 14.5% (P < 0.05), and event‐free survival was 60.0% vs. 76.3% (P < 0.05) for the balloon and stent group, respectively. Elective stent implantation in de novo SVG lesions is associated with a significant lower target vessel revascularization rate and a significant higher event‐free survival at 1‐year follow‐up as compared to balloon angioplasty. Catheter Cardiovasc Interv 2003;60:452–457. © 2003 Wiley‐Liss, Inc.
Delayed recovery of left ventricular function after recanalization of a chronic coronary occlusion
Authors: Werner Gerald S. , Betge Stefan , Küthe Friedhelm , Figulla Hans R.
Published: November 2003

An unusually prolonged course of recovery of severely impaired left ventricular (LV) function (EF 32%) was observed in a patient after recanalization of a chronically occluded LAD. Despite persistent vessel patency, LV function remained depressed for almost 2 years after the percutaneous transluminal coronary angioplasty until complete recovery (EF 82%) could be observed. The possibility of a delayed recovery should be considered when assessing new therapeutic strategies to improve LV function of chronically ischemic myocardium. Catheter Cardiovasc Interv 2003;60:491–495. © 2003 Wiley‐Liss, Inc.
Percutaneous transcatheter patent foramen ovale closure using the right internal jugular venous approach
Authors: Sader Mark A. , De Moor Michael , Pomerantsev Eugene , Palacios Igor F.
Published: November 2003

Percutaneous transcatheter closure of a patent foramen ovale (PFO) is a therapeutic option in patients with paradoxical embolism. For patients in whom PFO closure is indicated when a femoral venous approach is not possible, we describe the successful closure of two PFOs using the right internal jugular venous approach. Catheter Cardiovasc Interv 2003;60:536–539. © 2003 Wiley‐Liss, Inc.
Migraine with aura related to the percutaneous closure of an atrial septal defect
Authors: Rodés‐Cabau Josep , Molina Carlos , Serrano‐Munuera Carmen , Casaldáliga Jaume , Alvarez‐Sabin José , Evangelista Arturo , Soler‐Soler Jordi
Published: November 2003

We report a case of a 31‐year‐old woman who presented migraine attacks with aura within the 48 hr after transcatheter closure of an atrial septal defect with the Amplatzer septal occluder device. The migraine attacks persisted for 3 months, and all examinations performed to rule out a thromboembolic origin of migraine were negative. Catheter Cardiovasc Interv 2003;60:540–542. © 2003 Wiley‐Liss, Inc.
Developmental segregation in the efferent projections to auditory hair cells in the gerbil
Authors: Rontal Daniel A. , Echteler Stephen M.
Published: November 2003

The auditory receptor epithelium of mammals receives efferent innervation from neurons within and surrounding the superior olivary complex of the brainstem (Warr [1975] J. Comp. Neurol. 161:159–181). Disruption of this pathway during early postnatal life, when olivocochlear axons are forming their final connections with auditory hair cells and nerve fibers, can lead to profound and permanent hearing impairments (Walsh et al. [1998] J. Neurosci. 18:3859–3869). Identification of the possible causes for this deterioration in auditory function requires a better understanding of the normal developmental interactions that occur between efferent axons and their target cells within the cochlea. To provide such information, we labeled developing efferent fibers at a constant location within the gerbil cochlea by using the fluorescent carbocyanine dye 1,1′‐dioctadecyl‐3,3,3′,3′‐tetramethylindo‐carbocyanine perchlorate (DiI). The terminal arbors of these neurons were then reconstructed by using digital confocal microscopy. By postnatal day (P) 2, the efferent arbors associated with inner hair cells (IHCs) and outer hair cells (OHCs) displayed distinctly different morphologies closely resembling those described for adult animals (Brown [1987] J. Comp. Neurol. 260:605–619). Unlike their mature counterparts, however, P2 efferent axons frequently branched to contact both types of auditory hair cells. Unexpectedly, between P4 and P6, both IHC and OHC efferent axons produced additional branches that crossed the tunnel of Corti to invade the OHC zone. By P8, all of these supernumerary connections were eliminated, yielding completely segregated efferent pathways to IHCs and OHCs. J. Comp. Neurol. 467:509–520, 2003. © 2003 Wiley‐Liss, Inc.
Isoform‐specific distribution of the plasma membrane Ca2+ ATPase in the rat brain
Authors: Burette Alain , Rockwood Julia M. , Strehler Emanuel E. , Weinberg Richard J.
Published: November 2003

Regulation of cytoplasmic calcium is crucial both for proper neuronal function and cell survival. The concentration of Ca2+ in cytoplasm of a neuron at rest is 10,000 times lower than in the extracellular space, pointing to the importance of the transporters that extrude intracellular Ca2+. The family of plasma membrane calcium‐dependent ATPases (PMCAs) represent a major component of the Ca2+ regulatory system. However, little information is available on the regional and cellular distribution of these calcium pumps. We used immunohistochemistry to investigate the distribution of each of the four PMCA isoforms (PMCA1–4) in the rat brain. Each isoform exhibited a remarkably precise and distinct pattern of distribution. In many cases, PMCA isoforms in a single brain structure were differentially expressed within different classes of neurons, and within different subcellular compartments. These data show that each isoform is independently organized and suggest that PMCAs may play a more complex role in calcium homeostasis than generally recognized. J. Comp. Neurol. 467:464–476, 2003. © 2003 Wiley‐Liss, Inc.
Persistence of graded EphA/Ephrin‐A expression in the adult frog visual system
Authors: Bach Helene , Feldheim David A. , Flanagan John G. , Scalia Frank
Published: November 2003

Many studies have demonstrated the involvement of the EphA family of receptor tyrosine kinases and their ligands, ephrin‐A2 and ‐A5, in the development of the temporonasal axis of the retinotectal/collicular map, but the role of these molecules in optic nerve regeneration has not been well studied. Noting that the characteristic gradients of the EphA/ephrin‐A family that are expressed topographically in the retina and tectum of embryonic chicks and mice tend to disappear after birth, we took as our starting point an analysis of EphA and ephrin‐A expression in leopard frogs (Rana pipiens and utricularia), species capable of regenerating the retinotectal map as adults. For the EphA family to be involved in the regeneration, one would expect these topographic gradients to persist in the adult or, if downregulated after metamorphosis, to be reexpressed after optic nerve injury. Using EphA3 receptor and ephrin‐A5 ligand alkaline phosphatase in situ affinity probes (RAP and LAP, respectively) in whole‐mount applications, we report that reciprocally complementary gradients of RAP and LAP binding persist in the optic tract and optic tectum of postmetamorphic frogs, including mature adults. EphA expression in temporal retinal axons in the optic tract was significantly reduced after nerve section but returned during regeneration. However, ephrin‐A expression in the tectal parenchyma was not significantly elevated by either eye removal, with degeneration of optic axons, or during regeneration of the retinotectal projection. Thus, the present study has demonstrated a persisting expression of EphA/ephrin‐A family members in the retinal axons and tectal parenchyma that may help guide regenerating fibers, but we can offer no evidence for an upregulation of ephrin‐A expression in conjunction with optic nerve injury. J. Comp. Neurol. 467:549–565, 2003. © 2003 Wiley‐Liss, Inc.