A synthesis of the tricyclic core structure of FR901483 featuring an Ugi four-component coupling and a remarkably selective elimination reaction

Hirofumi Seike, Erik J. Sorensen

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

Three key reactions, an efficient Ugi four-component coupling, a regiospecific, base-mediated elimination reaction, and an intramolecular nitrone/alkene [3+2] cycloaddition, were used to achieve an effective synthesis of the tricyclic molecular framework of the immunosuppressant FR901483. The outcome of a control experiment supports the idea that an internal deprotonation by an alkoxide ion is the origin of the site selectivity observed in the base-induced elimination of hydroxy mesylate 17.

Original languageEnglish (US)
Pages (from-to)695-701
Number of pages7
JournalSynlett
Issue number5
DOIs
StatePublished - Mar 18 2008

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Keywords

  • Elimination reaction
  • Ugi four-component coupling
  • [3+2] cycloaddition

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