A practical, enantiospecific synthesis of (S)-trans-γ- monocyclofarnesol

Serra S.

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A practical, enantiospecific synthesis of (S)-trans-γ- monocyclofarnesol

机译：（S）-反式-γ-单环法尼醇的实用对映体合成

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An expedient and concise synthesis of (S)-trans-γ-monocyclofarnesol is here described. The aforementioned sesquiterpene was prepared starting from enantioenriched (S)-γ-dihydroionone, which was in turn obtained from racemic α-ionone through the combined use of two previously developed processes. Key steps of the presented synthesis are the stereoselective Horner-Wadsworth-Emmons reaction between triethyl phosphonoacetate and γ-dihydroionone and the effective fractional crystallization of the γ-monocyclofarnesol-3,5-dinitrobenzoate esters. By these means the target compound was obtained in good yield and with very high stereoisomeric purity.

机译：在此描述了一种简便且简明的（S）-反式-γ-单环法尼醇的合成。前述倍半萜烯是从对映体富集的（S）-γ-二氢紫罗兰酮开始制备的，该对映体又通过外消旋的α-紫罗兰酮通过结合使用两种先前开发的方法而获得。所提出的合成的关键步骤是膦酰基乙酸三乙酯和γ-二氢紫罗兰酮之间的立体选择性霍纳-沃兹沃思-埃蒙斯反应和γ-单环法尼醇-3,5-二硝基苯甲酸酯的有效分步结晶。通过这些手段，以高收率和非常高的立体异构体纯度获得目标化合物。

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《Natural product communications》 |2012年第12期|共4页
作者
Serra S.;
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正文语种 eng
中图分类自然科学总论;
关键词
Enzyme-mediated resolution; Fractional crystallization.; Horner-Wadsworth-Emmons reaction; Sesquiterpenes; Stereoselective synthesis;

机译：酶介导的拆分;碎片结晶;Horner-Wadsworth-Emmons反应;倍半萜烯;立体选择性合成;

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1. A practical, enantiospecific synthesis of (S)-trans-γ- monocyclofarnesol [J] . Serra S. Natural product communications . 2012,第12期

机译：（S）-反式-γ-单环法尼醇的实用对映体合成
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6. Studies on the Biosynthesis of Chetomin: Enantiospecific Synthesis of a Putative Late-Stage Biosynthetic Intermediate [O] . Timothy R. Welch, Robert M. Williams -1

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A practical, enantiospecific synthesis of (S)-trans-γ- monocyclofarnesol

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