Synthesis of the trans-hydrindane core of dictyoxetane

Benedicte Defaut, Thomas B. Parsons, Neil Spencer, Louise Male, Benson M. Kariuki, Richard S. Grainger

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

Abstract

A concise, stereoselective synthesis of the trans-hydrindane core of the marine natural product dictyoxetane is reported, starting from a Robinson annelation derived bicyclic enone. A phosphorane-mediated, pinacol-like rearrangement of a cis-diol, via a formal 1,2-hydride shift, is used to establish the requisite trans ring junction. 31P NMR supports the formation of the intermediate phosphorane, generated in situ from the reaction of a diol with Ph3PCl2.

Original languageEnglish
Pages (from-to)4926-4932
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number25
DOIs
Publication statusPublished - 7 Jul 2012

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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