Total synthesis of cryptophycins and their 16-(3-phenylacryloyl) derivatives

被引：45

作者：

Rej, R ^{[1
]}

Nguyen, D ^{[1
]}

Go, B ^{[1
]}

Fortin, S ^{[1
]}

Lavallee, JF ^{[1
]}

机构：

[1] BIOCHEM THERAPEUT INC,LAVAL,PQ H7V 4A7,CANADA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 18期

关键词：

D O I：

10.1021/jo960816b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cryptophycin A, a cyclic depsipeptide isolated from the blue-green alga (cyanobacterium) Nostoc sp.GSV 224, has shown excellent activity against solid tumors implanted in mice. The benzylic epoxide, which was shown to be very important for biological, activity, is also fairly unstable under both acidic and alkaline conditions. The high doses needed to observe in vivo activity might be a result of this instability. In order to solve this problem while preserving the electrophilic character of the benzylic position, enones 1 and 2 have been proposed as promising analogs of the natural product, and a convergent total synthesis of these compounds is described. In addition, the same strategy was used to prepare Cryptophycins A, B, C, and D.

引用

页码：6289 / 6295

页数：7