SYNTHESIS OF N-(TERT-BUTYLOXYCARBONYL)-CBI, CBI, CBI-CDPI1, AND CBI-CDPI2 - ENHANCED FUNCTIONAL ANALOGS OF CC-1065 INCORPORATING THE 1,2,9,9A-TETRAHYDROCYCLOPROPA[C]BENZ[E]INDOL-4-ONE (CBI) LEFT-HAND SUBUNIT

被引：161

作者：

BOGER, DL ^{[1
]}

ISHIZAKI, T ^{[1
]}

KITOS, PA ^{[1
]}

SUNTORNWAT, O ^{[1
]}

机构：

[1] UNIV KANSAS,DEPT BIOCHEM,LAWRENCE,KS 66045

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 23期

关键词：

D O I：

10.1021/jo00310a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Full details of the synthesis of N-(tert-butyloxycarbonyl)-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one [N-BOC-CBI (6)] constituting a more stable functional analogue of the CC-1065 left-hand subunit are described. The resolution of an immediate CBI synthetic precursor, (+)- and (—)-14, the unambiguous establishment of the absolute configuration, and the incorporation of (±)-, (+)-, and (—)-14 into the synthesis of racemic and optically active CBI (5), N-BOC-CBI (6), CBI-CDPI1(7), and CBI-CDPI2(8), enhanced functional analogues of CC-1065, are detailed. The chemical solvolytic behavior of the CBI-based agents and their cytotoxic properties are described. © 1990, American Chemical Society. All rights reserved.

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页码：5823 / 5832

页数：10

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