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Synthesis 2000; 2000(10): 1366-1368
DOI: 10.1055/s-2000-7107
short paper
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Synthesis of Cycloocta-3,5-dien-1-ol and Cycloocta-3,5-dien-1-one: SeO2/O2 Oxidation of Dienes

Elena S. Koltun* , Steven R. Kass
  • *Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA; Fax + 1(612)6 26 75 41; E-mail: kass@chem.umn.edu
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Publication Date:
31 December 2000 (online)

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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.

selenium oxide - oxygen - homoallylic alcohol - non-conjugated enone - oxidation

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