PROTECTING GROUP IMPROVEMENT BY ISOTOPIC-SUBSTITUTION - SYNTHESIS OF THE QUINONE SYSTEM OF FREDERICAMYCIN-A

被引：34

作者：

CLIVE, DLJ

CANTIN, M

KHODABOCUS, A

KONG, XL

TAO, Y

机构：

[1] Chemistry Department, University of Alberta, Edmonton

来源：

TETRAHEDRON | 1993年 / 49卷 / 36期

关键词：

D O I：

10.1016/S0040-4020(01)88016-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Use of a trideuteriomethyl group for protection of phenolic oxygen (as in 29, Scheme 4), instead of the classical methyl group, serves to suppress an unwanted intramolecular hydrogen transfer (12-->14, Scheme 2) during radical cyclization. The resulting spiro compound (31, Scheme 5) can be converted, by selective demethylation and oxidation, into a substance (35, Scheme 6) that represents the spirodiketone-quinone system of the antitumor agent Fredericamycin A.

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页码：7917 / 7930

页数：14

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