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.