A comparative study of the solvolysis reactivity, regioselectivity, and stereochemistry of the duocarmycin A and SA alkylation subunits

被引：30

作者：

Boger, DL

Goldberg, J

McKie, JA

机构：

[1] Department of Chemistry, Scripps Research Institute, San Diego, CA 92037

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1996年 / 6卷 / 16期

关键词：

D O I：

10.1016/0960-894X(96)00346-0

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The comparative solvolysis reactivity, regioselectivity, and stereochemistry of N-BOC-DSA (4) and N-BOC-DA (5), simple derivatives of the DNA alkylation subunits of duocarmycin SA and A, are detailed. Most important of the observations is the substantially greater reactivity of 5 versus 4 (16x), the modest regioselectivity of both 4 (6.5-4:1) and 5 (1.5:1), and the establishment that the abnormal ring expansion solvolysis proceeds by S(N)2 addition to the activated cyclopropane with clean inversion of the reacting center stereochemistry. Copyright (C) 1996 Elsevier Science Ltd

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页码：1955 / 1960

页数：6

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