Diastereoselective [2,3]-wittig rearrangement of a tertiary bisallylic ether

Xiongwei Shi, Francis X. Webster, James Kallmerten, Jerrold Meinwald

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Abstract

The diastereoselective [2,3]-Wittig rearrangement of a tertiary bisallylic ether (8) is described. The stereochemical outcomes for rearranged products were determined. The effects of reaction conditions on selectivities were investigated. Matsuccocus female sex pheromones 1-3 were efficiently synthesized via this rearrangement.

Original languageEnglish (US)
Pages (from-to)7197-7200
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number40
DOIs
StatePublished - Oct 2 1995

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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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