Divergent total synthesis of (-)-aspidophytine and its congeners via Fischer indole synthesis

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24 Citations (Scopus)

Abstract

A total synthesis of (-)-aspidophytine and the first total syntheses of its congeners, (+)-cimicidine and (+)-cimicine, were accomplished in a divergent manner. Construction of the aspidosperma skeleton was executed by Fischer indole synthesis between substituted phenylhydrazines and tricyclic aminoketone. The regiochemistry of the Fischer indole synthesis was strongly dependent on the choice of acid, and a weak acid, such as acetic acid provided the desired indolenine isomer in high selectivity.

Original languageEnglish
Pages (from-to)89-95
Number of pages7
JournalTetrahedron
Volume69
Issue number1
DOIs
Publication statusPublished - 2013 Jan 7

Keywords

  • Alkaloid
  • Aspidophytine
  • Fischer indole synthesis
  • Indolenine
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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