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Synthesis and odor of chiral partial structures of β‐vetivone. I.
Author(s) -
Spreitzer Helmut,
Piringer Iris,
Pichler Andrea,
Holzer Wolfgang,
Schreder Petra,
Widhalm Michael
Publication year - 1999
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1999)11:1<14::aid-chir3>3.0.co;2-7
Subject(s) - chemistry , enantiomer , diastereomer , chirality (physics) , circular dichroism , odor , absolute configuration , ionone , vibrational circular dichroism , stereochemistry , computational chemistry , organic chemistry , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
Several, stereoisomeric, monocyclic analogs of (−)‐β‐vetivone (1), one of the main constituents of vetiver oil, were studied to determine whether the olfactory properties of (−)‐β‐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. Chirality 11:14–20, 1999. © 1999 Wiley‐Liss, Inc.