bluuebunny/crossref_metadata_2025_split huggingface dataset:
4,13‐Diaza‐18‐Crown‐6
Authors: Gatto Vincent J. , Miller Steven R. , Gokel George W. 
Published: November 2003

Abstract

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

Abstract

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

Abstract

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

Abstract
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

Abstract

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

Abstract

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

Abstract

(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

AbstractAsymmetric hydrogenation of 3‐oxo carboxylates using binap‐ruthenium complexes: (R)‐(−)‐methyl 3‐hydroxybutanoatecatalyst: [(R)‐2,2′‐Bis(diphenylphosphino)‐1,1′‐binaphthyl]ruthenium(II) complexproduct: (R)‐(−)‐methyl 3‐hydroxybutanoate
2‐Methylene‐1,3‐Dithiolane
Authors: Dahnke Karl R. , Paquette Leo A. 
Published: November 2003

Abstract

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

Abstract

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

Abstract

(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

Abstract

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

Abstract

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

Abstract4‐dodecylbenzenesulfonyl azidesproduct: dodecylbenzenesulfonyl azides
1,3,5‐Cyclooctatriene
Authors: Oda Masaji , Kawase Takeshi , Kurata Hiroyuki 
Published: November 2003

Abstract

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

Abstract

(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

Abstract

[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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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
.
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

Abstract
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

Abstract(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 bromideproduct: (4R,5R)‐2,2‐Dimethyl‐α,α,α′,α′‐tetra(naphth‐2‐yl)‐1,3‐dioxolane‐4,5‐dimethanolintermediate: (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

Abstract(R,R)‐ and (S,S)‐N,N′‐dimethyl‐1,2‐diphenylethylene‐1,2‐diamineintermediate: N‐Methylbenzimineintermediate: meso‐ and dl‐N,N′‐Dimethyl‐1,2‐diphenylethylenediamineintermediate: dl‐N,N′‐Dimethyl‐1,2‐diphenylethylene‐diamineproduct: (R,R)‐(+)‐N,N′‐Dimethyl‐1,2‐diphenylethylenediamineproduct: (S,S)‐(−)‐N,N′‐Dimethyl‐1,2‐diphenylethylenediaminebyproduct: 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

Abstract

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

Abstract

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

Abstract

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

AbstractBromofluorination of alkenes: 1‐bromo‐2‐fluoro‐2‐phenylpropaneproduct: 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

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

Abstract

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

AbstractThis 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

AbstractOur 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

AbstractChronic 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

AbstractThis 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.