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Lactones 38: Synthesis and odoriferous properties of p ‐menthane lactones
Author(s) -
Dams Iwona,
Białońska Agata,
Ciunik Zbigniew,
Wawrzeńczyk Czesław
Publication year - 2012
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.3085
Subject(s) - chemistry , enantiomer , bicyclic molecule , hydrolysis , stereochemistry , lactone , organic chemistry
ABSTRACT An enantiomeric pair of bicyclic δ ‐lactones with the p ‐menthane system was obtained from enantiomerically pure isomers of (1 R ,2 S ,5 R )‐(–) and (1 S ,2 R ,5 S )‐(+)‐isopulegol. The Horner–Wadsworth–Emmons olefination of isopulegones followed by hydrolysis of esters and lactonization of acids were the key steps of the syntheses presented. The structures of the compounds were determined by both spectroscopic and crystallographic methods. Enantiomeric p ‐menthane esters and δ ‐lactones are characterized by interesting odoriferous properties. Copyright © 2012 John Wiley & Sons, Ltd.