VERSATILE SYNTHESIS OF TROPONES BY REACTION OF RHODIUM(II)-STABILIZED VINYLCARBENOIDS WITH 1-METHOXY-1-[(TRIMETHYLSILYL)OXY]BUTA-1,3-DIENE

被引：54

作者：

DAVIES, HML

CLARK, TJ

KIMMER, GF

机构：

[1] Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 22期

关键词：

D O I：

10.1021/jo00022a041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium(II)-catalyzed decomposition of vinyldiazomethanes in the presence of 1-methoxy-1-[(trimethylsilyl)oxy]buta-1,3-diene leads to [3 + 4] annulation products by a tandem cyclopropanation/Cope rearrangement sequence. The resulting cycloheptadienes are readily converted to cycloheptatrienones either by hydrolysis with mild acid followed by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone or by treatment with dichloroethoxyoxovanadium. The efficiency of the general strategy was demonstrated through a short synthesis of nezukone.

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页码：6440 / 6447

页数：8

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