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J Org Chem. 2013 Jun 21;78(12):6154-62. doi: 10.1021/jo4007943. Epub 2013 Jun 13.

Transannular reductive rearrangement of α-amino ketones: construction of aza-tricyclic frameworks of several alkaloids.

Author information

1
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, PR China.

Abstract

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.

PMID:
23724931
DOI:
10.1021/jo4007943

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