Synthesis of the trans-hydrindane core of dictyoxetane

Research output: Contribution to journalArticle

Authors

  • Benedicte Defaut
  • Neil Spencer
  • Louise Male

Colleges, School and Institutes

External organisations

  • Cardiff University

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.

Details

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