Geometry-selective synthesis of the unsaturated side chains of the isodomoic acids

Nadia Fleary-Roberts, Gilles Lemière, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

2 Citations (Scopus)

Abstract

Abstract Three unsaturated vinylic or allylic halides were made in enantiomerically pure form, ready for coupling with a vinyl metal as part of a divergent strategy for the synthesis of members of the domoic/isodomoic acid family and their analogues. The trisubstituted alkene 3 was made by an E-selective Wittig reaction, while 4 and 5 were made by stereoselective hydrometallation or hydroboration of an alkyne.

Original languageEnglish
Pages (from-to)7204-7208
Number of pages5
JournalTetrahedron
Volume71
Issue number39
Early online date20 Feb 2015
DOIs
Publication statusPublished - 30 Sep 2015

Keywords

  • Alkene
  • Coupling
  • Metalcatalysed
  • Natural product synthesis

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