Novel synthetic approach to (S)-coriolic acid

被引：28

作者：

Babudri, F ^{[1
]}

Fiandanese, V ^{[1
]}

Marchese, G ^{[1
]}

Punzi, A ^{[1
]}

机构：

[1] Univ Bari, Dipartmento Chim, Ctr CNR Studio Metodol Innovat Sintesi Organ, I-70126 Bari, Italy

来源：

TETRAHEDRON | 2000年 / 56卷 / 02期

关键词：

silicon and compounds; stereoselective synthesis; natural products;

D O I：

10.1016/S0040-4020(99)01003-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthetic approach to (S)-coriolic acid 1 has been developed, starting from the readily available (E)-1-bromo-2-trimethylsilylethene 4 and trimethylsilylacetylene 5. A simple acylation reaction of 4, followed by a coupling reaction of the halogenoderivative intermediate with 5 in the presence of a Pd(0) catalyst affords the monosilylated ketoenyne 7. After desilylation of 7, enantioselective reduction of the carbonyl group with (S)-BINAL-H leads to the alcohol 2 (e.c.=94%). A subsequent coupling reaction and stereoselective reduction of the triple bond affords the target molecule 1. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：327 / 331

页数：5

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