Total synthesis of (+)-sieboldine A: evolution of a pinacol-terminated cyclization strategy

SM Canham, DJ France…

文献索引：Canham, Stephen M.; France, David J.; Overman, Larry E. Journal of Organic Chemistry, 2013 , vol. 78, # 1 p. 9 - 34

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被引用次数: 20

摘要

This article describes synthetic studies that culminated in the first total synthesis of the Lycopodium alkaloid sieboldine A. During this study, a number of pinacol-terminated cationic cyclizations were examined to form the cis-hydrindanone core of sieboldine A. Of these, a mild Au (I)-promoted 1, 6-enyne cyclization that was terminated by a semipinacol rearrangement proved to be most efficient. Fashioning the unprecedented N- ...