SYNTHESIS AND CHEMISTRY OF DYNEMICIN-A MODELS

被引：112

作者：

NICOLAOU, KC ^{[1
]}

SMITH, AL ^{[1
]}

WENDEBORN, SV ^{[1
]}

HWANG, CK ^{[1
]}

机构：

[1] UNIV CALIF SAN DIEGO, DEPT CHEM, LA JOLLA, CA 92093 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1991年 / 113卷 / 08期

关键词：

D O I：

10.1021/ja00008a045

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of the model systems 10 and 22 of dynemicin A (2) containing the nitrogen, enediyne, and epoxide functionalities has been achieved. These models are shown to undergo acid-induced triggering to give the corresponding Bergman-cyclized products in the presence of suitable H atom donors. Removal of the N protecting group from 22 gave the unstable free amine 30, which was shown to cause double-stranded-DNA cleavage, presumably in a manner similar to that of dynemicin A (2) itself. Some interesting chemistry related to dicobalt complexes of the enediynes is also presented.

引用

页码：3106 / 3114

页数：9