Sporidesmins. Part XI. The reaction of triphenylphosphine with epipolythiodioxopiperazines

S. Safe, A. Taylor

Research output: Contribution to journalArticle

23 Scopus citations

Abstract

Dehydrogliotoxin and sporidesmin react with triphenylphosphine to give an epithiodioxopiperazine and triphenylphosphine sulphide. The reaction involves epimerization of the asymmetric centres of the dioxopiperazine ring. The epithiodioxopiperazines from sulphoxides when treated with peracids and these compounds are racemic. Evidence is presented, which suggests, that the reaction of sporidesmin E with triphenylphosphine occurs primarily at the sulphur-bound sulphur atom and that one conformation of this trisulphide reacts preferentially to the other.

Original languageEnglish (US)
Pages (from-to)1189-1192
Number of pages4
JournalJournal of the Chemical Society C: Organic Chemistry
DOIs
StatePublished - 1971

ASJC Scopus subject areas

  • Organic Chemistry

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