Five-Step Total Synthesis of (±)-Aspidospermidine by a Lactam Strategy via an Azomethine Ylide

Seiya Katahara, Yasukazu Sugiyama, Mina Yamane, Yukinori Komiya, Takaaki Sato, Noritaka Chida

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

A five-step total synthesis of (±)-aspidospermidine (1) based on a lactam strategy is reported. Our synthesis features an iridium-catalyzed reductive Michael addition/[3+2] cycloaddition cascade to give a tricyclic ketone intermediate from a simple lactam via an azomethine ylide. The developed strategy enables easily available lactams to be used as stable surrogates of multisubstituted amines and would be applicable to a unified total synthesis of complex Aspidosperma alkaloids.

Original languageEnglish
Pages (from-to)3058-3063
Number of pages6
JournalOrganic Letters
Volume23
Issue number8
DOIs
Publication statusPublished - 2021 Apr 16

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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