Total synthesis of the immunosuppressant FR901483 via an amidoacrolein cycloaddition

Research output: Contribution to journalArticle

64 Scopus citations

Abstract

Matrix presented The total synthesis of the potent immunosuppressant FR901483 is described. In a key step, the intermolecular Diels-Alder cycloaddition of an amidoacrolein with 2-(triisopropylsilyloxy)-1,3-butadiene produced the desired 3-cyclohexene-1-carboxaldehyde. This compound was subjected to basic followed by acidic conditions which effected two sequential aldol cyclizations to deliver the tricyclic ring system of the natural product, suitably functionalized for completion of the total synthesis.

Original languageEnglish (US)
Pages (from-to)1125-1128
Number of pages4
JournalOrganic Letters
Volume3
Issue number8
DOIs
Publication statusPublished - Apr 19 2001

    Fingerprint

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this