Enantiospecific synthesis, separation and olfactory evaluation of all diastereomers of a homologue of the sandalwood odorant Polysantol®

被引：29

作者：

Castro, JM ^{[1
]}

Linares-Palomino, PJ ^{[1
]}

Salido, S ^{[1
]}

Altarejos, J ^{[1
]}

Nogueras, M ^{[1
]}

Sánchez, A ^{[1
]}

机构：

[1] Univ Jaen, Fac Ciencias Expt, Dept Quim Inorgan & Organ, Jaen 23071, Spain

来源：

TETRAHEDRON | 2005年 / 61卷 / 47期

关键词：

alpha-campholenic aldehyde derivatives; alpha-pinene; enantiospecific synthesis; organoleptic evaluation; sandalwood; odorants;

D O I：

10.1016/j.tet.2005.09.023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The four stereoisomers of (5E)-4,4-dimethyl-6-(2',2,3'-trimethylcyclopent-3'-en-1'-yl)-hex-5-en-3-ol, a homologue of the valuable sandalwood-type odorant Polysantol (R), were enantiospecifically synthesized from (+)- and (-)-alpha-pinene, through (-)- and (+)-campholenic aldehyde, by aldol condensation with 3-pentanone, deconjugative a-methylation and reduction. The mixtures of epimeric, alcohols obtained after reduction were separated by means of derivatization with (-)-(1S)-camphanic chloride. The enantiomerically pure final products were evaluated organoleptically. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：11192 / 11203

页数：12

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