A general synthetic route towards γ- and δ-lactones.: Total asymmetric synthesis of (-)-muricatacin and the mosquito oviposition pheromone (5R,6S)-6-acetoxy-hexadecanolide.

被引：46

作者：

Couladouros, EA

Mihou, AP

机构：

[1] Agr Univ Athens, Dept Chem, Athens 11855, Greece

[2] NCSR Demokritos, Organ & Bioorgan Chem Lab, Athens 60228, Greece

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 26期

关键词：

D O I：

10.1016/S0040-4039(99)00895-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Five (or six) membered asymmetric lactones are synthesized from gamma-butyrolactone (or delta-valerolactone) in a straightforward way using the following reaction sequence: reduction, Wittig-Schlosser coupling, Sharpless asymmetric dihydroxylation, oxidation and lactonization. Thus, (-)-muricatacin is synthesized in six steps (43 % overall yield). Furthermore, (5R,6S)-6-acetoxy-hexadecanolide is prepared in eight steps (38 % overall yield) via a carbonate ester, utilizing a novel lactonization with inversion of stereochemistry. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：4861 / 4862

页数：2

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