bluuebunny/crossref_metadata_2025_split huggingface dataset:
Biosynthesis of the Cytochalasans. Part III. 13C‐NMR. of cytochalasin B (phomin) and cytochalasin D. Incorporation of [1‐13C]‐ and [2‐13C]‐sodium acetate
Authors: Graf Werner , Robert Jean‐Louis , Vederas John C. , Tamm Christoph , Solomon Philippa H. , Miura Iwao , Nakanishi Koji 
Published: December 2004

AbstractSequential single frequency decoupling and partially relaxed Fourier transform (PRFT) are used to assign the natural abundance 13C‐NMR. spectra of cytochalasin B (phomin) (1) and cytochalasin D (2). Cultures of Phoma spec. S 298 were fed [2‐13C]‐sodium acetate, and the distribution of this precursor in cytochalasin B (phomin) (1) was determined by 13C‐NMR. spectroscopy. Likewise, the labelling patterns in cytochalasin D (zygosporin A) (2) from Zygos‐posium masonii could be identified after incorporation of [2‐13C]‐sodium acetate and [l‐13C]‐sodium acetate. The results confirm previous proposals for the biogenesis of the cytochalasans from phenylalanine, methionine, and a C18, or C16, polyketide part.
Photochemische Reaktionen. 78. Mitteilung. Anwendung der π → π*‐induzierten Cyclisierung von α,β‐ungesättigten γ‐Dimethoxymethylketonen auf 19‐Methoxy‐ bzw. 19‐Dimethoxy‐Steroid‐enone und ‐dienone
Authors: Karvaš Milan , Marti Franz , Wehrli Hansuli , Schaffner Kurt , Jeger Oskar 
Published: December 2004

AbstractIrradiation at 254 nm of 19‐dimethoxyandrost‐4‐en‐17 β‐ol‐3‐one acetate (8) afforded the epimeric cyclization products 9 (yield 20%) and 10 (4%). Similar transformations were also achieved with the analogous dimethoxy‐enone 24 (→ 25, 65%), and‐dienone 30 (→ 31, 72%), and with the methoxy‐enone 33 (→ 34, 30%), and‐dienone 35 (→ 36, 17%).
1‐Fluoro‐benzocyclopropenium Ion from 1,1‐difluoro‐benzocyclopropene
Authors: Burger Ulrich , Müller Paul , Zuidema Laura 
Published: December 2004

Abstract1,1‐Difluoro‐benzocyclopropene (1) ionizes in fluorosulphonic acid to yield the cation 2, which is stable at − 50° for several hours. Upon quenching with water 2 affords benzoic acid.
Hormone‐Receptor Interactions. Demonstration of Two Message Sequences (Active Sites) in α‐Melanotropin
Authors: Eberle Alex , Schwyzer Robert 
Published: December 2004

AbstractThe purpose of this investigation was to elucidate the biological significance of the tripeptide sequence 11–13, ‐Lys‐Pro‐Val · NH2 contained in α‐melanocyte‐stimulating hormone. To this end the in vitro melanotropic activities of 21 synthetic peptides related to the hormone were determined and compared with one‐another and with results reported in the literature. The tripeptide amide, H · Lys‐Pro‐Val · NH2, its Nα‐acetylderivative, and ‐weakly, but distinctly‐Nα‐acetyl‐L‐lysine‐amide were found to be hormonally active. The following conclusions were drawn: (1) α‐melanophore‐stimulating hormone possesses two message sequences (active sites), ‐Met‐Glu‐His‐Phe‐Arg‐Trp‐Gly‐, and ‐Lys‐Pro‐Val · NH2 which are capable of independently triggering the hormone receptor responsible for melanin dispersion. (2) In correct covalent combination, the two message sequences act in a ‘cooperative’ manner to potentiate their activities on the receptors. (3) ‐Lys‐Pro‐Val‐ is an address sequence in adrenocorticotropic hormone and a message sequence in α‐melanocyte‐stimulating hormone. This implies that the two receptors (adrenal and melanocyte), albeit recognizing ‐Met‐Glu‐His‐Phe‐Arg‐Trp‐Gly‐ as stimulus, differ fundamentally in their response to ‐Lys‐Pro‐Val‐.
Comments on the Interpretation of NMR. Parameters in some platinum‐olefin complexes
Authors: Pregosin Paul S. , Venanzi L. M. 
Published: December 2004

Abstract13C and 195Pt‐NMR. parameters for the complexes trans‐[PtCl2(C5H10N)‐(CH3CHCHCH3)] are presented. It is suggested that conclusions, concerning metal olefin bond strengths, drawn from NMR. studies of nuclei not directly involved in the bonding can be misleading.
Total Synthesis of Indole and Dihydroindole Alkaloids. VIII. Studies on the synthesis of bisindole alkaloids in the vinblastine‐vincristine series. The chloroindolenine approach
Authors: Kutney James P. , Beck John , Bylsma Feike , Cook James , Cretney Walter J. , Fuji Kaoru , Imhof René , Treasurywala Adi M. 
Published: December 2004

AbstractStudies on the syntheses of 18′‐epi‐4′‐deoxo‐4′‐epivinblastine (IX, R = CO2CH3; R1 = H), 18′‐decarbomethoxy‐18′‐epi‐4′‐deoxo‐4′‐epivinblastine (IX, R = R1 = H) and related analogues are described. The synthetic method employs a coupling reaction involving chloroindolenine derivatives of the cleavamine series (for example, III) with vindoline (V) under acidic conditions. The complete structures, including absolute configuration, of the resulting dimers are established by a combination of chemical and spectroscopic techniques, including X‐ray analysis.
Ylides du soufre dérivés de sucres Communication préliminaire
Authors: Tronchet Jean M. J. , Eder Hansjörg 
Published: December 2004

AbstractS‐Methylation of 6‐S‐benzyl‐6‐deoxy‐1,2‐O‐isopropylidene‐3‐O‐methyl‐α‐D‐xylo‐6‐thiohexofuranos‐5‐ulose (1) gave the expected sulfonium salt 2 which on alcaline treatment yielded the stable sulfur ylide 3. This compound constitutes an useful synthetic intermediate in carbohydrate chemistry. On heating in 1,2‐dimethoxyethane, it underwent a Stevens rearrangement which led to an extension of the carbon chain of the sugar and, reacted with Michael acceptors, it gave cyclopropanation reactions.
Regiospecific Intramolecular Aldol Condensation Induced by Conjugate Addition of lithium dimethylcuprate to ζ‐Oxo‐α, β‐enones preliminary communication [1]
Authors: Näf Ferdinand , Decorzant René , Thommen Walter 
Published: December 2004

Abstractζ‐Oxo‐α, β‐enones react with lithium dimethylcuprate to give cyclic aldols such as hydroxydecalone 1 and hydroxyspiro[4.5]decanone 2 in a regio‐ and stereospecific manner. This new reaction, a combination of conjugate methyl addition to α, β‐enones with directed intramolecular aldolisation, is suggested to proceed via either enoate anions, such as 8 and 11, or radical anions, such as 9 → 10 and 12 → 13, as intermediates.
Weitreichende Kernspin‐Kopplungen in 2‐Fluorbenzamiden II. [15N]‐2‐Fluorbenzamid
Authors: Fritz Hans , Winkler Tammo , Küng Werner 
Published: December 2004

AbstractLarge ‘through space’ hydrogen‐fluorine and 15N, F‐couplings have been observed in [15N]‐2‐fluorbenzamide. The nuclear spin information is transmitted via the hydrogen bond between fluorine and the trans‐NH‐proton of the amide group, as shown by the solvent dependence of the couplings.
7. Azidiniumsalze. 19. Mitteilung [1]. Einführung der Diazogruppe in reaktive Methylenverbindungen mit Azidiniumsalzen
Authors: Balli Heinz , Löw Richard , Müller Volkmar , Rempfler Hermann , Sezen‐Gezgin Ayten 
Published: December 2004

Diazo‐Group Transfer to Active Methylene Compounds Using Azidinium SaltsDie Synthese von Diazoverbindungen durch Diazogruppenübertragungen auf durch Carbonyl‐, Cyan‐ und Nitro‐Gruppen aktivierte Methylenverbindungen mit den Azidiniumsalzen 2‐Azido‐3‐äthyl‐benzthiazolium‐tetrafluoroborat und 1‐Äthyl‐2‐azido‐pyridinium‐tetrafluoroborat wird beschrieben.
9. Azidiniumsalze. 21. Mitteilung [1]. Einführung der Diazogruppe in Amino‐arene und Amino‐hetarene mit Azidiniumsalzen: Synthese kondensierter ν‐Triazole
Authors: Balli Heinz , Felder Louis 
Published: December 2004

Diazo‐Group Transfer to Amino‐arenes and Amino‐hetarenes Using Azidinium Salts: Synthesis of 1, 2, 3‐TriazolesDas Azidiniumsalz 2‐Azido‐3‐äthyl‐benzthiazolium‐tetrafluoroborat (1) lässt sich als Diazogruppenüberträger auf Amino‐arene und Amino‐hetarene einsetzen. Die primär entstandenen Diazoniumsalze cyclisieren sich zu kondensierten ν‐Triazolen bzw. kuppeln mit den Edukten zu o, o′‐Diamino‐azofarbstoffen.
Zur Imidazolbildung aus 2H‐Azirinen bzw. Vinylaziden und Nitrilen unter Säurekatalyse
Authors: Bader Heinz , Hansen Hans‐Jürgen 
Published: December 2004

Acid‐Catalysed Formation of Imidazoles from 2H‐Azirines or Vinylazides and NitrilesThe reaction of 2H‐azirines with nitriles in the presence of boron trifluoride etherate to yield the corresponding imidazoles is described. 2,3‐Diphenyl‐2H‐azirine (10) gives 2‐substituted 4,5‐diphenyl imidazoles in moderate bis good yields (seeTable 1). The reaction of10with acrylonitrile only leads to the formation of 4,5‐diphenyl‐2‐vinylimidazole (17). No products resulting from an addition to the C,C double bond are observed. 2H‐Azirine10and ethyl cyanoacetate yield the expected imidazole18(30%) but also 2‐cyanomethyl‐4,5‐diphenyloxazole (20; 7%) (seeScheme 4). The yield of imidazole formation mainly depends on the substituents in position 2 of the 2H‐azirines (seeScheme 6), a change of the substitutents in position 3 having only little influence. The best yields are observed with a phenyl group at C(2) of the 2H‐azirines. These observations are in agreement with the occurrence of 1‐azaallyl cations formed by ring opening of the 2H‐azirines linked to theLewisacid (boron trifluoride). Similar results are obtained with the corresponding vinyl azides with the exception of 1‐azido‐1‐phenylethylene (28). Whereas the corresponding 3‐phenyl‐2H‐azirine (24) gives 2,4‐diphenylimidazole (33;Scheme 6) in the presence of benzonitrile and boron trifluoride etherate, the azide28yields only acetanilide (86%). In the presence of triethyloxonium tetrafluoroborate 2H‐azirines and benzonitrile react to yield the corresponding 1‐ethylimidazoles (seeScheme 9). This again demonstrates that 1‐azaallyl cations must be intermediates which react with the nitrile presumably in aRittertype reaction.13C‐NMR. spectra of 2H‐azirines are also reported(Table 2).
Composants volatils de la «mousse de chêne» (Evernia Prunastri (L.) ACH.) 3e communication
Authors: Gavin José , Nicollier Gilles , Tabacchi Raffaele 
Published: December 2004

Volatiles constituents of “Oakmoss”(Evernia Prunastri (L.) ACH.)The chemical consititution of different fractions of two oakmoss oleoresines were investigated by GC./MS. using SCOT. and capillary columns. Besides many known compounds, over 52 (sesquiterpenes, aliphatic and aromatic hydrocarbons) have not yet been reported as constituents of oakmoss.
3,4‐Dimethoxyfuran: Eigenschaften, Berechnungen und Substitutionsreaktionen
Authors: Iten Peter Xaver , Hofmann Alfred André , Eugster Conrad Hans 
Published: December 2004

3,4‐Dimethoxyfuran: Properties, Calculations and some Substitution Reactions3,4‐Dimethoxyfuran (3,4‐DF) is much more reactive than furan itself. We present experimental details for the synthesis of this useful compound in 50–100 g batches. 3‐4‐Dibenzyloxyfuran has also been prepared. Quantum mechanical calculations by PPP‐and CNDO‐methods analogous to furan itself gave the following information (compared with furan): enhanced negative partial charge at C(2) and C(5), higher acidity at α‐position, a stronger and at the same time inverted dipol moment. In accordance with the calculations, 3,4‐DF can easily be substituted by weak electrophilic reagents, e.g. in a typical Mannich reaction. The bis‐amino compound 8 is produced in good yields. Lithiation by butyl‐Li leads to mono‐ or di‐substituted products. The mono‐ and di‐Li‐3,4‐DF have been used for the preparation of various acylated and alkylated 3,4‐DF derivatives.By acid hydrolysis of 3,4‐DF crystalline 4‐methoxy‐3 (2H)‐furanone has been prepared.
Kinetics of Extremely Fast Ligand Exchange Reactions with Methylmercury(II)‐complexes of 1‐Methylpyridine‐2‐thione and 1‐Methyl‐quinaldine‐4‐thione: Rate‐Equilibria Correlations
Authors: Erni Isidor , Geier Gerhard 
Published: December 2004

AbstractMethylmercury(II) transfer from two heterocyclic thiones to a wide variety of other ligands and the reverse reaction have been investigated by the temperature‐jump method. The reactions are almost diffusion controlled, even when the free energy difference is negligible. The only exceptions are reactions to and from hydroxide. They are about hundred times slower than those with other ligands of comparable stability at zero free energy difference. This is in agreement with the behaviour of hydroxide in other methylmercury(II) exchange reactions. They follow an associative reaction mechanism. An empirical correlation of rate‐and equilibrium‐constants for atom transfer reactions is proposed. This equation shows some similarities to that of the Marcus type for atom transfer. However, the proposed equation not only describes reactions governed by an associative mechanism, but also those of dissociative type and cases between the two extremes.
Metal complexes with macrocyclic ligands. XIII. The complexation of Cu2+ with triazacycloalkanes
Authors: Riedo Theodor J. , Kaden Thomas A. 
Published: December 2004

AbstractThe potentiometric study of the complexation of Cu2+ with 1,4,7‐triazacyclononane (1), 1,4,8‐triazacyclodecane (2) 1,5,9‐triazacyclododecane (3) has shown that CuL, CuL2 and (CuLOH)2 are the main species present in solution. Their stabilities (Table 1) and their absorption spectra (Table 2) indicate facial coordination of the cyclic triamines in a distorted octahedral geometry.The formation and dissociation kinetics have been measured by stopped‐flow techniques. The formation in acetate buffer can be described by the reaction of Cu2+ and CuAcO+ with the monoprotonated species of the ligand. The bimolecular rate constants for these complexations (Table 3) decrease when the ring size increases. In contrast the dissociation induced by acid is only little affected by the ring size. Thus for these complexes the rate of formation and not that of the dissociation determines the overall stability.
Umlagerungsreaktionen an 11a‐Aminomethyl‐hexahydromorphanthridin‐6(5H)‐onen
Authors: Süess Rudolf 
Published: December 2004

Intramolecular transamidation reactions of 11a‐aminomethyl‐hexahydromorphanthridin‐6(5H)‐onesThe methane sulfonic esters, 7A,B of cis‐ and trans‐11a‐hydroxymethyl‐hexahydromorphanthridin‐6(5H)‐one 6A,B rearrange when treated with primary amines forming 2′‐amino‐3,5‐dihydro‐2‐methylspiro [2‐benzazepine‐4(4H), 1′‐cyclohexane]‐1(2H)‐ones 9A,B. The structural change involves an intramolecular trans‐amidation of the intermediates 8A,B. The original morphanthridine skeleton may be recovered by a second rearrangement, with concurrent reduction, induced by lithium aluminium hydride.
Nucleotide. IX. Synthese und Eigenschaften von 1‐(2′‐Desoxy‐D‐ribofuranosyl)‐lumazin‐3′‐monophosphaten
Authors: Charubala Ramamurthy , Pfleiderer Wolfgang 
Published: December 2004

Nucleotides. IX. Synthesis and properties of 1‐(2′‐deoxy‐D‐ribofuranosyl)‐lumazin‐3′‐monophosphatesThe synthesis of various 1‐(2′‐deoxy‐α‐[and β‐]D‐ribofuranosyl)‐lumazine‐3′‐monophosphates 25‐‐30 starting from the corresponding pteridine nucleosides 1‐‐6 is described. Monomethoxytritylation in 5′‐position to 7‐‐12, phosphorylation by cyanoethylphosphate to 13‐‐18, and deprotection by acid and base treatment afforded the lumazine nucleotides 25‐‐30 in good overall yield. The various reaction products have been characterized by physical means, such as UV. spectra, pK‐values and their chromatographical and electrophoretical behaviour. Enzymatic dephosphorylations by alkaline phosphatase led to the starting material 1‐‐6 with a 3‐‐4 times slower hydrolysis rate in comparison to Tp.
Reaktionen der valenzpolaromeren Ketenform mesoionischer Heterocyclen mit 3‐Dimethylamino‐2H‐azirinen
Authors: Lukáč Josef , Heimgartner Heinz 
Published: December 2004

Reactions of valencepolaromeric ketenes of mesoionic heterocyles with 3‐dimethylamino‐2H‐azirinesReactions of the 3‐dimethylamino‐2H‐azirines 1a and 1b with the mesoionic oxazole 5 and the mesoionic dithiole 6 in acetonitrile at room temperature yield the 1:1 adducts 11, 12, 19 and 20, respectively (Schemes 5 and 8). These products can be formulated as adducts of the aminoazirines and the ketenes 5a and 6a, which are valence polaromeric forms of the mesoionic heterocycles 5 and 6 (Scheme 2).The structure of the adducts has been elucidated by spectral data and their comparison with the data of (Z)‐11, the structure of which has been established by X‐ray [19]. Oxidation of the 1:1 adducts with KMnO4 in a two‐phase system yields 4‐dimethylamino‐3‐oxazolin‐2‐ones (cf. Scheme 6) by clevage of the exocyclic C,C‐double bond. A mechanism for the formation of the adducts is given in Scheme 9: Nucleophilic attack of 1 on the ketene leads to a primary adduct of type a, which undergoes clevage of the former N(1), C(2)‐azirine bond to give adducts of type 11 or 19. The N(1), C(2)‐ring opening of 1a in the reaction with ketenes contrasts with the N(1), C(3)‐opening of 1a in the addition with, for instance, isothiocyanates. These different ring openings are explained by the difference in nucleophilicity of the heteroatoms X and Y in a′ (Scheme 10).
Minor and Trace Sterols in Marine Invertebrates. XII. Occurrence of 24 (R + S)‐isopropenylcholesterol, 24 (R + S)‐methylcholesta‐5, 25‐dien‐3β‐ol, and 24 (R + S)‐methylcholesta‐7, 25‐dien‐3β‐ol in the caribbean sponge, Verongia cauliformis
Authors: Kokke W. C. M. C. , Pak C. S. , Fenical William , Djerassi Carl 
Published: December 2004

AbstractIn addition to the two new sterols verongulasterol 11 and 25‐dehydroaplysterol 13 of Verongia cauliformis3), which were reported earlier [2] [3], the minor and trace sterols of this sponge include five new sterols listed in the title (with the exception of the known 24 S‐methyl‐cholesta‐5, 25‐dien‐3β‐ol (codisterol, 1b). The isolation of the 24(R)‐epimer of codisterol is of interest, as this compound is a possibly biosynthetic precursor for aplysterol 12, 25‐dehydroaplysterol 13, and verongulasterol 11 (all 24R) which occur in the same sponge [2]. A partial synthesis from fucosterol (4) of 24 (R + S)‐isopropenylcholesterol (9), and of 24‐isopropylcholesterol (10) is described.
Synthesis of 5‐Methyluridine and Its 5′‐Mercapto‐, 2‐Amino‐, and 4′,5′‐Unsaturated Analogues
Authors: Škarié Vinko , Matulié‐Adamié Jasenka 
Published: December 2004

AbstractThe stereospecific cis‐hydroxylation of 1‐(2,3‐dideoxy‐β‐D‐glyceropent‐2‐enofuranosyl)thymine (1) into 1‐β‐D‐ribofuranosylthymine (2) by osmium tetroxide is described. Treatment of 2′,3′‐O, O‐isopropylidene‐5‐methyl‐2,5′‐anhydrouridine (8) with hydrogen sulfide or methanolic ammonia afforded 5′‐deoxy‐2′,3′‐O, O‐isopropylidene‐5′‐mercapto‐5‐methyluridine (9) and 2′,3′‐O, O‐isopropylidene‐5‐methyl‐isocytidine (10), respectively. The action of ethanolic potassium hydroxide on 5′‐deoxy‐5′‐iodo‐2′,3′‐O, O‐isopropylidene‐5‐methyluridine (7) gave rise to the corresponding 1‐(5‐deoxy‐β‐D‐erythropent‐4‐enofuranosyl)5‐methyluracil (13) and 2‐O‐ethyl‐5‐methyluridine (14).The hydrogenation of 2 and its 2′,3′‐O, O‐isopropylidene derivative 4 over 5% Rh/Al2O3 as catalyst generated diastereoisomers of the corresponding 5‐methyl‐5,6‐dihydrouridine (17 and 18).
Stabilité dans le méthanol et propriétés thermodynamiques de transfert des cryptates de certains cations de transition et de métaux lourds
Authors: Spiess Par Bernard , Arnaud‐Neu Françoise , Schwing‐Weill Marie‐José 
Published: December 2004

Stability in Methanol and Thermodynamic Transfer Properties of the Cryptates of some Transition Cations and Heavy MetalsThe nature and stability of the macrocyclic and macrobicyclic complexes of Ag+, Cd2+, and Pb2+ (Mn+) with 21, 22, 211, 221 and 222 in anhydrous methanol 0.05M in Et4N+ClO−4, at 25° (see Scheme) have been determined by potentiometry and spectrophotometry. Binuclear complexes M2L2n+ have been observed in all cases, besides the mononuclear MLn+ complexes. The macrobicyclic 1:1 complexes MLn+ exhibit an important ‘cryptate effect’ with Mn+=Ag+, Pb2+ and Cd2+, but not with Cu2+ and Zn2+; their stability is in all cases maximum with 221.The applicability to our results of the recent extrathermodynamic hypothesis involving MLn+ cryptates is examined.
Die Reaktion von Phthalaldehyden mit 3‐Nitropropionsäureestern. Ein einfacher Zugang zu 3‐Nitro‐2‐naphthoesäuren
Authors: Kienzle Frank 
Published: December 2004

The Reaction of Phthalaldehydes with 3‐Nitropropionates. A Simple Route to 3‐Nitro‐2‐naphthoic Acids3‐Nitro‐propionates condense with phthalaldehydes and related compounds in the presence of a base to give 3‐nitro‐2‐naphthoic acids.
Photochemische Reaktionen. 116. Mitteilung [1]. Notiz zur 1γ, δ*‐induzierten Photospaltung von γ, δ‐Epoxy‐eucarvon
Authors: Tsutsumi Kentaro , Wolf Hans Richard 
Published: December 2004

π, π*‐Induced Photocleavage of γ, δ‐Epoxy‐eucarvone.On 1π, π*‐excitation 1 undergoes cleavage of the C, C‐oxirane bond (1 → c) and isomerizes to the bicyclic dihydrofurane compound 5. In addition, 1 shows photocleavage of the C (γ), O‐oxirane bond (1 → d) and gives the isomers 2, 3, 6, 7 and 8. Furthermore, the cyclohexenone 9 and the cyclohexene‐1, 4‐dione 10 are formed presumably via an intermediate 13, which could also arise from d. Besides these products the compounds 11 and 12 are obtained, which are photoproducts of 2.
Synthesis and Absolute Configuration of Naturally Occurring Dactyloxene‐B and ‐C
Authors: Maurer Bruno , Hauser Arnold , Ohloff Günther 
Published: December 2004

AbstractNatural (+)‐dactyloxene‐B (12) and ‐C (13) have been synthesized starting from (+)‐trans‐2, 5, 6‐trimethyl‐l‐cyclohexene‐l‐carbaldehyde (1) which is shown to have the (5S, 6R)‐configuration by chemical correlation with (+)‐(2R, 3S, 6S)‐2, 3, 6‐trimethylcyclohexanone. The absolute configurations are therefore (2R, 5R, 9S, 10R) for (+)‐dactyloxene‐B and (2R, 5S, 9S, 10R) for (+)‐dactyloxene‐C.
Synthesis of cannabinoid model compounds. Part 2: (3R, 4R)‐Δ1(6)‐Tetrahydrocannabinol‐5″‐oic acid and 4″(R, S)‐Methyl‐(3R, 4R)‐Δ1(6)‐tetrahydrocannabinol‐5″‐oic Acid
Authors: Franke Ingo , Binder Michael 
Published: December 2004

AbstractTwo novel cannabinoid model compounds, (3R, 4R)‐Δ1(6)‐tetrahydrocannabinol‐5″‐oic acid (22) and 4″(R, S)‐methyl‐(3R, 4R)‐Δ1(6)‐tetrahydrocannabinol‐5″‐oic acid (23) were synthesized by acid‐catalyzed condensation of (+)‐trans‐p‐mentha‐2, 8‐dien‐l‐ol (1) with the substituted resorcinols 18 and 19 obtained by a Wittig reaction between 3, 5‐bis(benzyloxy)benzaldehyde (7) and methyl 4‐bromobutanoate (10) or methyl 4‐bromo‐2(R, S)‐methylbutanoate (11) resp. with subsequent hydrogenation. The resulting methyl esters 20 and 21 were hydrolyzed to give acids 22 and 23.
Studies Related to Biological Detoxification of Kraft Pulp Mill Effluent. IV.The Biodegradation of 14‐Chlorodehydroabietic Acid with Mortierella isabellina
Authors: Kutney James P. , Dimitriadis Eugene , Hewitt Gary M. , Salisbury Philip J. , Singh Mahatam , Servizi James A. , Martens Dennis W. , Gordon Robert W. 
Published: December 2004

AbstractOne of the fish‐toxic chlorinated resin acids, 14‐chlorodehydroabietic acid (5), found in kraft mill effluent is examined. When exposed to the fungus Mortierella isabellina, 5 is converted into a number of hydroxylated derivatives which show low levels of toxicity to fish. These biotransformation products were isolated and characterized.
Studies related to biological detoxification of kraft pulp mill effluent. V. The synthesis of 12‐ and 14‐chlorodehydroabietic acids and 12,14‐dichlorodehydroabietic acid, fish‐toxic diterpenes from kraft pulp mill effluent
Authors: Kutney James P. , Dimitriadis Eugene 
Published: December 2004

AbstractAn improved synthesis of the isomeric 12‐ and 14‐chlorodehydroabietic acids (3 and 2, respectively) and 12,14‐dichlorodehydroabietic acid (4) is described. The monochioro isomers were conveniently separated as the imidazole derivatives, and conversion of the latter to the free acids or their corresponding methyl esters could be achieved in high yield. Studies involving microbial degradation of 2–4 are underway.