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Synlett 1996; 1996(4): 349-350
DOI: 10.1055/s-1996-5421
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Synthesis of α-Farnesene Hydroperoxides

Simon Fielder1 , Daryl D. Rowan, Michael S. Sherburn2
  • 1Horticulture and Food Research Institute of New Zealand Ltd, Private Bag 11030, Palmerston North, New Zealand
  • 2Department of Chemistry and Biochemistry, Massey University, Private Bag 11222, Palmerston North, New Zealand
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Publication History

Publication Date:
31 December 2000 (online)

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A short and efficient synthetic route to two sesquiterpene autoxidation products is presented. The successful strategy involved converting geraniol into conjugated trienyl hydroperoxide (3). This cyclised efficiently in the presence of oxygen and an initiator to afford the very labile endoperoxy hydroperoxide (5), a route which mimics α-farnesene autoxidation.

hydroperoxide - endoperoxide - synthesis - α-farnesene - autoxidation