OXIDATION AND ALKYLATION OF SPECTINOMYCIN DERIVATIVES - SYNTHESIS OF TROSPECTOMYCIN FROM SPECTINOMYCIN

被引：17

作者：

HERRINTON, PM

KLOTZ, KL

HARTLEY, WM

机构：

[1] The Upjohn Company, Kalamazoo

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 03期

关键词：

D O I：

10.1021/jo00055a021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trospectomycin can be prepared in five steps from spectinomycin. The overall yield of the process is 13.3%. The synthesis involves a new oxidation of silyl enol ether 4 to enone 5 by use of an alkyl hydroperoxide. This reaction is mild and very selective, giving excellent yields. The synthesis also involves a gamma-alkylation of enone 5 activated by a beta-oxygen. This alkylation is unusual in that no alkylation is seen at the a (4') carbon.

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页码：678 / 682

页数：5

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