Synthesis and odor of chiral partial structures of β-vetivone, Part 2

✍ Scribed by Helmut Spreitzer; Iris Piringer; Andrea Pichler; Wolfgang Holzer; Jana Ruzicka; Michael Widhalm

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 132 KB
• Volume: 11
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/(sici)1520-636x(1999)11:2<133::aid-chir9>3.0.co;2-e

✦ Synopsis

Several stereoisomeric, monocyclic analogs of (-)-␤-vetivone (1), one of the main constituents of vetiver oil, were studied to examine if 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 studied. 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 whereas absolute configurations were determined by circular dichroism (CD) methods.