SYNTHESIS OF CBI-PDE-I-DIMER, THE BENZANNELATED ANALOG OF CC-1065

被引：79

作者：

ARISTOFF, PA

JOHNSON, PD

机构：

[1] Medicinal Chemistry Research, Upjohn Company, Kalamazoo

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 23期

关键词：

D O I：

10.1021/jo00049a035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical synthesis of CBI (2), utilizing inexpensive starting materials, was developed and applied to the synthesis of benzannelated analogs of CC-1065, in particular CBI-PDE-I-dimer (13) and CBI-bis-indole (17). While a Sharpless asymmetric dihydroxylation reaction proved effective at providing optically active intermediates, a more classical resolution procedure was used to prepare materials of higher optical purity. A novel cyclization employing a six-membered-ring intermediate (12) was employed to construct the cyclopropyl ring in CBI. Like CC-1065, CBI-PDE-I-dimer appears to cause delayed toxicity in mice.

引用

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页码：6234 / 6239

页数：6

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