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 journalArticle

11 Citations (Scopus)

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

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Ketones
Alkaloids

ASJC Scopus subject areas

  • Organic Chemistry

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Transannular reductive rearrangement of α-amino ketones : Construction of aza-tricyclic frameworks of several alkaloids. / Zhang, Jian; Wang, Yong Qiang; Wang, Xin Wei; Li, Wei Dong Z.

In: Journal of Organic Chemistry, Vol. 78, No. 12, 21.06.2013, p. 6154-6162.

Research output: Contribution to journalArticle

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