1080-67-7Relevant articles and documents
The role of germacrene D as a precursor in sesquiterpene biosynthesis: Investigations of acid catalyzed, photochemically and thermally induced rearrangements
Buelow, Nils,Koenig, Wilfried A
, p. 141 - 168 (2007/10/03)
Germacrene D is considered as a precursor of many sesquiterpene hydrocarbons. We have investigated the acid catalyzed as well as the photochemically and thermally induced rearrangement processes of germacrene D isolated from several Solidago species, which contain both enantiomers of germacrene D. Enantiomeric mixtures of sesquiterpenes of the cadinane, eudesmane (selinane), oppositane, axane, isodaucane, and bourbonane group as well as isogermacrene D were identified as main products and made available as reference compounds for structure investigations and stereochemical assignments of plant constituents. δ-Amorphene, one of the rearrangement products, was identified as a natural product for the first time. The absolute configuration of γ-amorphene was revised by correlation with the absolute configuration of germacrene D. The mechanisms of the rearrangement reactions are discussed. (C) 2000 Elsevier Science Ltd.
Asymmetric Intramolecular Ene Reaction Catalyzed by a Chiral Titanium Reagent and Synthesis of (-)-ε-Cadinene
Narasaka, Koichi,Hayashi, Yujiro,Shimada, Satoru,Yamada, Jun
, p. 261 - 271 (2007/10/02)
A highly diastereo- and enantio-selective intramolecular ene reaction was developed by employing a chiral titanium reagent generated in situ from TiCl2(OPri)2 and a tartrate-derived chiral 1,4-diol.This reaction afforded masked cyclohexanone an
Stereoisomeric ε-Dienes of the Cadalane Series: Synthesis and Configurational Correlation
Koester, Frank-Hinrich,Wolf, Herbert,Kluge, Heinz
, p. 78 - 92 (2007/10/02)
rac-ε-Cadinene (1) and rac-ε-amorphene (4) were prepared by Wittig reaction of the diketones 9 and 10, obtained by ?-cyclization (7->8), and alternatively from the keto alcohols 11b and 12b. rac-ε-bulgarene (3) was prepared from the ene-ol 15b, available from 11b by Wittig reaction via epimerization.The ketones 10 and 12b are not epimerizable, so rac-ε-muurolene (2) was obtained from the enone 24, accessible by Diels-Alder reaction (21 + 22 ->23). - Configurational assignments of 1 - 4 and of the bicyclic precursors are confirmed by the 13C-NMR spectra supported by 2D-INADEQUATE experiments.