Stereoselective formation of a β-lactam fused oxathiazepin: A synthetic approach to eudistomins

Tohru Yamashita, Hidetoshi Tokuyama, Tohru Fukuyama

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

A synthetic approach to eudistomin via a β-lactam fused bicyclic oxathiazepin intermediate is described. A β-lactam fused oxathiazepin derivative was synthesized by intramolecular 7-membered oxime ether formation and subsequent face-selective reduction of the C-N double bond. A fully functionalized orthoalkenylphenylthioanilide bearing oxathiazepin ring was then prepared and construction of the indole skeleton under several radical-mediated conditions was examined.

Original languageEnglish
Pages (from-to)738-740
Number of pages3
JournalSynlett
Issue number5
Publication statusPublished - 2003 May 1
Externally publishedYes

Keywords

  • 2,3-disubstituted indole
  • Bicyclic β-lactam
  • Eudistomin
  • Oxathiazepin
  • Radical cyclization

ASJC Scopus subject areas

  • Organic Chemistry

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