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

✍ Scribed by Helmut Spreitzer; Iris Piringer; Andrea Pichler; Wolfgang Holzer; Petra Schreder; Michael Widhalm

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
146 KB
Volume
11
Category
Article
ISSN
0899-0042

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✦ Synopsis

Several, stereoisomeric, monocyclic analogs of (-)-␤-vetivone (1), one of the main constituents of vetiver oil, were studied to determine whether the olfactory properties of (-)-␤-vetivone (1) could be reproduced from these structurally simpler, synthetically accessible compounds. The effects of diastereomeric and enantiomeric structural differences on the odor of the partial vetivone structure were determined. A chiral phenyl sulfoximine was used for separation of the racemic mixtures. Detailed nuclear magnetic resonance (NMR) spectroscopic studies ( 1 H, 13 C) were used to determine relative configurations while absolute configurations were determined by circular dichroism (CD) methods.

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