Transannular Reductive Rearrangement of α-Amino Ketones: Construction of Aza-tricyclic Frameworks of Several Alkaloids

作者：Jian Zhang, Yong‐Qiang Wang, Xinwei Wang, Wei‐Dong Z. Li · 发表于：The Journal of Organic Chemistry · 年份：2013 · DOI：10.1021/jo4007943 · 被引用次数：31 · 研究领域：Chemical synthesis and alkaloids、Advanced Synthetic Organic Chemistry、Alkaloids: synthesis and pharmacology

Transannular reductive rearrangement of bridged cyclic α-amino ketones led to the aza-tricyclic frameworks azepinoindole, hydrolulolidine, and hydrojulolidine of the typical alkaloids of Stemona, Aspidosperma, and Lycopodium, respectively. This facile approach demonstrates the potential applicability of the Clemmensen-Clemo-Prelog-Leonard reductive rearrangement of tricyclic α-amino ketones for the aza-heterocycle synthesis.