A bismuth(III)-catalyzed friedel-crafts cyclization and stereocontrolled organocatalytic approach to (-)-platensimycin

Stanley T.C. Eey, Martin James Lear

Research output: Contribution to journalArticlepeer-review

60 Citations (Scopus)

Abstract

A high yielding route to the (-)-platensimycin core is communicated. This entailed the discovery of Bi(OTf)3 to catalyze a Friedel-Crafts cyclization of a free lactol, supplemented by LiClO4 to suppress the Lewis basicity of the sulfonate group. After TBAF-promoted cyclodearomatization, a diastereoselective conjugate reduction of a dienone was achieved by adopting amine-based organocatalytic rationales to reverse the inherent steric control of the substrate.

Original languageEnglish
Pages (from-to)5510-5513
Number of pages4
JournalOrganic letters
Volume12
Issue number23
DOIs
Publication statusPublished - 2010 Dec 3

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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