106777-57-5Relevant articles and documents
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.