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

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posted on 21.06.2013 by Jian Zhang, Yong-Qiang Wang, Xin-Wei Wang, Wei-Dong Z. Li
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.