SYNTHESIS OF (+/-)-FERRUGININE AND (+/-)-ANHYDROECGONINE METHYL-ESTER BY A TANDEM CYCLOPROPANATION COPE REARRANGEMENT

被引:136
作者
DAVIES, HML
SAIKALI, E
YOUNG, WB
机构
[1] Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109
关键词
D O I
10.1021/jo00019a044
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rhodium(II) acetate catalyzed decomposition of vinyldiazomethanes in the presence of N-(alkoxycarbonyl)pyrroles led to the synthesis of 8-azabicyclo[3.2.1]octa-2,6-dienes. The vinylcarbenoids generated from vinyldiazomethanes with a single electron-withdrawing group exhibited competing reactivity at the vinyl terminus in addition to the carbenoid site. Good regiocontrol was possible, however, by appropriate choice of catalyst and solvent. The practicality of this new approach to tropane alkaloids was demonstrated through short syntheses of (+/-)-ferruginine, (+/-)-anhydroecgonine methyl ester, and the lower homologue of (+/-)-anatoxin a.
引用
收藏
页码:5696 / 5700
页数:5
相关论文
共 49 条