Stereocontrolled total synthesis of (-)-eudistomin C

Tohru Yamashita, Nobutaka Kawai, Hidetoshi Tokuyama, Tohru Fukuyama

Research output: Contribution to journalArticlepeer-review

63 Citations (Scopus)

Abstract

A stereocontrolled total synthesis of (-)-eudistomin C was accomplished in 18-step sequence with an overall yield of 7.7%. The synthesis features the diastereoselective Pictet-Spengler reaction of a tryptamine derivative and the Garner aldehyde catalyzed by Bronsted acids, and the unprecedented construction of the unusual oxathiazepine ring by intramolecular alkylation.

Original languageEnglish
Pages (from-to)15038-15039
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number43
DOIs
Publication statusPublished - 2005 Nov 2
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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