Synthesis and odor of chiral partial structures of beta-vetivone. I.

Several, stereoisomeric, monocyclic analogs of (-)-beta-vetivone (1), one o f the main constituents of vetiver oil, were studied to determine whether t he olfactory properties of (-)-beta-vetivone (1) could be reproduced from t hese structurally simpler, synthetically accessible compounds. The effects of diastereomeric and enantiomeric structural differences on the odor of th e partial vetivone structure were determined. A chiral phenyl sulfoximine w as used for separation of the racemic mixtures. Detailed nuclear magnetic r esonance (NMR) spectroscopic studies (H-1, C-13) were used to determine rel ative configurations while absolute configurations were determined by circu lar dichroism (CD) methods. Chirality 11:14-20, 1999. (C) 1999 Wiley-Liss, Inc.