A practical synthesis of the lipophilic side chain of the polyoxypeptins

被引：16

作者：

Lorca, M ^{[1
]}

Kurosu, M ^{[1
]}

机构：

[1] Florida State Univ, Dept Chem, Tallahassee, FL 32306 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(01)00205-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The lipophilic side chain of the cyclic depsipeptide polyoxypeptin A (1) and B (2), strong apoptosis inducers, has been synthesised as an ester of mixed methyl ketal 18. The key step is an asymmetric anti-aldol reaction of the designed 2-(N-2-methylbenzyl-N-2,4,6-trimethylbenzyl) amino-1-phenylpropyl ester 8 by means of a combination of LDA-Cp2ZrC2 (0.3 equiv.) for enolation and transmetallation into the zirconium enolate for aldolization. By using a non-boron associated anti-aldol reaction, 10 g of the key lactone 6 were synthesised in six steps from 8 and in 48% overall yield. (C) 2001 Published by Elsevier Science Ltd.

引用

页码：2431 / 2434

页数：4

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