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

Jian Zhang, Yong Qiang Wang, Xin Wei Wang, Wei Dong Z. Li

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)6154-6162
Number of pages9
JournalJournal of Organic Chemistry
Volume78
Issue number12
DOIs
StatePublished - Jun 21 2013

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Transannular reductive rearrangement of α-amino ketones: Construction of aza-tricyclic frameworks of several alkaloids'. Together they form a unique fingerprint.

Cite this