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Keywords:

  • terpenoid lactones; p-menthanolides; isopulegol; odorous compounds; lactonization

ABSTRACT

An enantiomeric pair of bicyclic δ-lactones with the p-menthane system was obtained from enantiomerically pure isomers of (1R,2S,5R)-(–) and (1S,2R,5S)-(+)-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.