Synthesis of the C21-C34-segment of the aplyronines using the dimer of methylketene

被引：19

作者：

Calter, MA ^{[1
]}

Guo, X ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

TETRAHEDRON | 2002年 / 58卷 / 35期

基金：

美国国家卫生研究院;

关键词：

methylketene dimer; aplyronine; Wittig reaction;

D O I：

10.1016/S0040-4020(02)00723-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This report describes a convergent synthesis of the C-21-C-34-segment of aplyronine. The starting point for both halves of this segment was the dimer of methylketene, readily available in either enantiomeric form by asymmetric catalysis. Diastereoselective reduction and functional group manipulation afforded the partners for a Wittig coupling reaction. The appropriate choice of oxygen protecting groups allowed the Wittig reaction to proceed, and hydrogenation of the resulting olefin afforded the C-21-C-34-synthon. (C) 2002 Elsevier Science Ltd. All rights reserved.

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收藏

页码：7093 / 7100

页数：8

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