Stereocontrolled total synthesis of (-)-aspidophytine

Shinjiro Sumi, Koji Matsumoto, Hidetoshi Tokuyama, Tohru Fukuyama

Research output: Contribution to journalArticlepeer-review

66 Citations (Scopus)

Abstract

The enantioselective stereocontrolled total synthesis of aspidophytine is described. The key indole intermediate was prepared by radical cyclization of 2-alkenylphenylisocyanide, followed by Sonogashira-coupling with a highly functionalized terminal acetylene. The 11-membered cyclic amine, a precursor for the formation of the aspidosperma skeleton, was synthesized using nitrobenzenesulfonamide chemistry. After construction of the pentacyclic skeleton, the lactone ring was formed to complete the total synthesis.

Original languageEnglish
Pages (from-to)8571-8587
Number of pages17
JournalTetrahedron
Volume59
Issue number43
DOIs
Publication statusPublished - 2003 Oct 20
Externally publishedYes

Keywords

  • Aspidophytine
  • Aspidosperma alkaloid
  • Indole
  • Macrocycles
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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