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Synlett 2001; 2001(5): 0661-0663
DOI: 10.1055/s-2001-13359
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A Concise Synthesis of Fumagillol

Martin Hutchings* , David Moffat, Nigel S. Simpkins
  • *The School of Chemistry, The University of Nottingham, University Park, Nottingham, NG7 2RD U.K.; E-mail: nigel.simpkins@nottingham.ac.uk
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Publication History

Publication Date:
31 December 2001 (online)

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A concise synthesis of fumagillol was accomplished in twelve steps starting from cyclohexadiene, proceeding by way of ring-opening of a symmetrical protected epoxydiol with a cuprate reagent and subsequent protecting group manipulation to give a key ketone intermediate. Installation of the required epoxide functions was achieved by addition of chloromethyllithium to the ketone and by directed epoxidation of the unsaturated side-chain.

fumagillol - stereoselective synthesis - epoxides - cuprate