Cyclopentane Construction with Control of Side Chain Configuration: Enantioselective Synthesis of (+)-Brefeldin A

Douglass F. Taber, Lee J. Silverberg, Edward D. Robinson

Research output: Contribution to journalArticle

60 Scopus citations

Abstract

Intramolecular opening of an enantiomerically pure epoxide by an amide enolate (1 → 2) is shown to be an effective method for cyclopentane construction with control of both ring and side chain absolute configuration. This opening serves as the key step in a synthesis of the Golgi apparatus-blocking macrolide (+)-brefeldin A (3). Other features of the synthesis include improved procedures for the enantioselective hydrogenation of a β-keto ester to the corresponding β-hydroxy ester, and for the Julia-Lythgoe reduction of a β-acetoxy sulfone to the trans alkene.

Original languageEnglish (US)
Pages (from-to)6639-6645
Number of pages7
JournalJournal of the American Chemical Society
Volume113
Issue number17
DOIs
StatePublished - Aug 1 1991

All Science Journal Classification (ASJC) codes

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

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