Synthesis of cycloocta-3,5-dien-1-ol and cycloocta-3,5-dien-1-one: SeO2/O2 oxidation of dienes

E. S. Koltun, S. R. Kass

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Abstract

A useful synthesis of cycloocta-3,5-dien-1-ol was developed starting from cycloocta-1,3-diene. Oxidation of the diene with selenium oxide in refluxing acetic anhydride affords the homoallylic and allylic acetates in a 19:1 ratio and a 36% overall yield when O2 is bubbled through the reaction mixture. Subsequent reduction with LAH affords the homoallylic alcohol (95%), which can be readily oxidized via TPAP/N-MMO (73%) to the corresponding non-conjugated dienone. This route represents the most efficient method for the preparation of cycloocta-3,5-dien-1-ol and cycloocta-3,5-dien-1-one reported to date, and may provide a general approach to the synthesis of homoallylic alcohols and non-conjugated enones.

Original languageEnglish (US)
Pages (from-to)1366-1368
Number of pages3
JournalSynthesis
Issue number10
DOIs
StatePublished - Jan 1 2000

Keywords

  • Homoallylic alcohol
  • Non-conjugated enone
  • Oxidation
  • Oxygen
  • Selenium oxide

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