Communication

Second-Generation Synthesis of Azadirachtin: A Concise Preparation of the Propargylic Mesylate Fragment†

  1. Alistair Boyer Dr.,
  2. Gemma E. Veitch Dr.,
  3. Edith Beckmann Dr.,
  4. Steven V. Ley Prof. Dr.

Article first published online: 12 JAN 2009

DOI: 10.1002/anie.200805395

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 48, Issue 7, pages 1317–1320, February 2, 2009

Additional Information

How to Cite

Boyer, A., Veitch, Gemma E., Beckmann, E. and Ley, Steven V. (2009), Second-Generation Synthesis of Azadirachtin: A Concise Preparation of the Propargylic Mesylate Fragment. Angew. Chem. Int. Ed., 48: 1317–1320. doi: 10.1002/anie.200805395

Author Information

  1. Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW (UK), Fax: (+44) 1223 336442

  1. †

    We gratefully acknowledge the EPSRC (A.B. and G.E.V.) and the Alexander von Humboldt Foundation (E.B.) for funding.

Publication History

  1. Issue published online: 28 JAN 2009
  2. Article first published online: 12 JAN 2009
  3. Manuscript Received: 4 NOV 2008

Funded by

  • EPSRC
  • Alexander von Humboldt Foundation

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Keywords:

  • α-keto lactones;
  • asymmetric catalysis;
  • hetero Diels–Alder reaction;
  • natural products;
  • total synthesis

Abstract

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A second bite of the apple: A new and highly efficient synthesis of the propargylic mesylate fragment of azadirachtin has been accomplished (see scheme; Bn=benzyl, Ms=methanesulfonyl, PMB=para-methoxybenzyl, TBDPS=tert-butyldiphenylsilyl). An enantioselective catalytic hetero Diels–Alder reaction sets up the stereocenter at C15, which then controls the installation of the remaining functionality in a total of only 17 steps.

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