Synthesis of 2,3-disubstituted indoles by radical cyclization with hypophosphorous acid and its application to total synthesis of (±)-catharanthine

Matthew T. Reding, Yosuke Kaburagi, Hidetoshi Tokuyama, Tohru Fukuyama

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

Radical cyclization of o-alkenylthioanilides using hypophosphorous acid and AIBN in the presence of Et3N proceeded smoothly to furnish the corresponding 2,3-disubstituted indoles in high yields. Utilizing the newly developed cyciization condition, a stereocontrolled total synthesis of (±)-catharanthine has been completed.

Original languageEnglish
Pages (from-to)313-330
Number of pages18
JournalHeterocycles
Volume56
Issue number1-2
DOIs
Publication statusPublished - 2002 Jan 1
Externally publishedYes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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