Stereoselective synthesis of the 5,5-difluoro-(12R)- and -(125)-leukotrienes B3

Vijaya Lingam Manthati, Danielle Grée, René Grée

Research output: Contribution to journalArticle

19 Scopus citations

Abstract

The first synthesis of the 5,5-difluoro-(12R)- and -(12S)-leukotrienes B3 is reported which uses a flexible and convergent strategy. The key steps involve a Sonogashira coupling between the bromodienone 4 and the propargylic difluoride 5; this is followed by a CBS type reduction to establish the (12R) or (12S) stereocenters. A final semihydrogenation, under controlled conditions, affords the required E,E,Z trienic system.

Original languageEnglish (US)
Pages (from-to)3825-3829
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number17
DOIs
StatePublished - Aug 26 2005

Keywords

  • Eicosanoids
  • Enantioselectivity
  • Fluorine
  • Leukotrienes
  • Stereoselective synthesis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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