Electrophilic cyclization of 1,6-dienes containing an allylsilane moiety -: Enantioselective synthesis of cis- and trans-γ-irone

被引：16

作者：

Beszant, S ^{[1
]}

Giannini, E ^{[1
]}

Zanoni, G ^{[1
]}

Vidari, G ^{[1
]}

机构：

[1] Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 20期

关键词：

fragrances; terpenoids; total synthesis; synthetic methods; cyclization;

D O I：

10.1002/ejoc.200300276

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper, we report the first examples of Lewis acid and mercuric trifluoroacetate promoted cyclizations of 1,6-dienes containing an allylsilane moiety. Mercuric trifluoro acetate has been proved to be the reagent of choice leading to methylenecyclohexane derivatives in good yields and with complete regioselectivity albeit with poor diastereoselectivity. Using this methodology a stereodivergent synthesis of enantiomerically pure (-)-(2S,6R)-cis-gamma-irone and (-)-(2S,6S)trans-gamma-irone, two precious aroma constituents, has been accomplished. This represents an innovative approach with respect to previous syntheses of gamma-irones. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

引用

页码：3958 / 3968

页数：11

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