Rapid access to epothilone analogs via semisynthetic degradation and reconstruction of epothilone D

被引：19

作者：

Dong, SD ^{[1
]}

Sundermann, K ^{[1
]}

Smith, KMJ ^{[1
]}

Petryka, J ^{[1
]}

Liu, FH ^{[1
]}

Myles, DC ^{[1
]}

机构：

[1] Kosan Biosci, Dept Chem, Hayward, CA 94545 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 09期

关键词：

epothilone; epothilone analogs; degradation; semisynthesis; ring closing metathesis;

D O I：

10.1016/j.tetlet.2003.12.123

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient route to epothilone analogs has been developed from the natural product epothilone D (1). Degradation of 1 via an oxidative cleavage sequence provides acid intermediate 4 rapidly in six steps. From 4, a variety of epothilone analogs have been prepared utilizing ring-closing metathesis to reconstruct the trisubstituted-12,13-double bond. Using this approach, we report a number of epothilone analogs with varying C-15 aromatic side chains and C-14 allylic substitutions and their biological activities. (C) 2004 Elsevier Ltd. All rights reserved.

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页码：1945 / 1947

页数：3

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