Lactones. 21. † Synthesis and Odoriferous Properties of Lactones with the p-Menthane System

Starting from (R)-(+)- and (S)-(−)-pulegone, enantiomeric pairs of esters and lactones with the p-menthane system were obtained. The Claisen rearrangement of allylic alcohols and iodolactonization of γ,δ-unsaturated acids were the key steps of syntheses presented. The structures of compounds were de...

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Veröffentlicht in:	Journal of agricultural and food chemistry 2004-03, Vol.52 (6), p.1630-1634
Hauptverfasser:	Dams, Iwona, Białońska, Agata, Ciunik, Zbigniew, Wawrzeńczyk, Czesław
Format:	Artikel
Sprache:	eng
Schlagworte:	Aroma and flavouring agent industries Biological and medical sciences Crystallography, X-Ray Food industries Fundamental and applied biological sciences. Psychology Lactones - chemical synthesis Lactones - chemistry Magnetic Resonance Spectroscopy Mentha - chemistry Molecular Structure Monoterpenes Odorants - analysis Oils, Volatile - chemistry Stereoisomerism Terpenes
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Beschreibung
Zusammenfassung:	Starting from (R)-(+)- and (S)-(−)-pulegone, enantiomeric pairs of esters and lactones with the p-menthane system were obtained. The Claisen rearrangement of allylic alcohols and iodolactonization of γ,δ-unsaturated acids were the key steps of syntheses presented. The structures of compounds were determined by both spectroscopic and crystallographic methods. Some of the synthesized compounds are characterized by interesting odoriferous properties. Keywords: Terpenoid lactones; p-menthanolides; pulegone; odorous compounds; Claisen rearrangement; iodolactonization; dehalogenation
ISSN:	0021-8561 1520-5118
DOI:	10.1021/jf035272a