Journal ArticleDOI
Über die Herstellung von Äther der enantio‐14, 15‐Dinorlabdan‐Reihe aus Eperusäure
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The conversion of Eperuic acid into Ethers of the enantio-14, 15-Dinorlabdane Series is described in this article, where the enantiomers 7 and 8, hitherto unknown, have been synthesized from EperUic acid (4) and their olfactory properties compared with those of 5 and 6.Abstract:
The Conversion of Eperuic Acid into Ethers of the enantio-14, 15-Dinorlabdane Series
5 and 6 are strongly odiferous substances of the ambra-type. Their enantiomers 7 and 8, hitherto unknown, have been synthesized from eperuic acid (4) and their olfactory properties compared with those of 5 and 6. 4 was esterified by CH2N2 and dehydrogenated with (C6H5Se)2/H2O2 to the α,β-unsaturated ester 9 (61%). Oxidation by KMnO4 in acetone yielded the ketone 3 (60%). Epoxidation followed by treatment with acid converted 3 into the acetals 7 (61%) and 8 (14%). 7 and 8 differ from 5 and 6 in odor intensity, and 6 and 8 show slightly different odor quality.read more
Citations
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Significance of the Geminal Dimethyl Group in the Odor Principle of Ambrox
TL;DR: The diastereoisomeric 18-nor and 19-norambrox ((6α)- and (6β)-dodecahydro-3a,6,9a-trimethylnaphtho[2,1-b]furans resp.) as well as the corresponding 18,19-dinor-derivatives have been synthesized and subjected to sensory evaluation as discussed by the authors.
Journal ArticleDOI
Asymmetric alkylation of α-aryl substituted carbonyl compounds by means of chiral phase transfer catalysts. Applications for the synthesis of (+)-podocarp-8(14)-en-13-one and of (−)-Wy-16,225, a potent analgesic agent
Wim Nerinckx,Maurits Vandewalle +1 more
TL;DR: Asymmetric induction in the alkylation (alkyl halides and enones) of α-aryl substituted ketones, esters and lactones by means of CPTC has been evaluated as discussed by the authors, and the potential of the method is illustrated by the asymmetric synthesis of (+)-podocarp-8(14)-ene-13-one (13 ) and of (−)-Wy-16,225 (10 ), a bridged aminotetralin with potent analgesic properties.
Journal ArticleDOI
13C-NMR data of diterpenes isolated from Aristolochia Species.
TL;DR: This work presents a compilation of the 13C-NMR data of 57 diterpenoids described between 1981 and 2007 which were isolated from Aristolochia species.
References
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Journal ArticleDOI
Odor Incongruity and Chirality
Lester Friedman,John G. Miller +1 more
TL;DR: The enantiomers R-(-)- and S-(+)-carvone are the organoleptic constituents in oil of spearmint and caraway, respectively and their odor distinctiveness has been unambiguously demonstrated by chemical interconversion, independent synthesis, and resolution.
Journal ArticleDOI
Optisch aktives β-Citronellol aus (+)- oder (−)-Pinan
Roland Rienäcker,G. Ohloff +1 more
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Hydrogen-deuterium exchange kinetics of the C-2 protons of imidazole and histidine compounds.
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Synthesis of potential ambra odorants: 5,5,9-trimethyldecalyl derivatives.
TL;DR: A novel general one-step synthesis of 2-decalones by means of acid catalyzed cyclization of acyclic or monocyclic precursors has been developed.