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Synthesis 1996; 1996(5): 652-666
DOI: 10.1055/s-1996-4254
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A Synthesis of (+)-Herboxidiene A

Nicholas D. Smith, Philip J. Kocienski* , Stephen D. A. Street
  • *Department of Chemistry, The University, Southampton, SO17 1BJ, UK, Fax +44(01703)678825; E-mail pjk1@soton.ac.uk
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Publication Date:
31 December 2000 (online)

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Key steps in a stereoselective synthesis of Herboxidiene A, a diastereoisomer of the natural herbicide Herboxidiene, include a Hoppe homoaldol reaction, a copper(I)-mediated 1,2-metallate rearrangement, and a one-pot synthesis of a diene fragment from condensation of a lithiated benzothiazolyl sulfone and an aldehyde.

herbicide - 1,2-metallate rearrangement - organocuprate - homoaldol reaction - Julia olefination - directed epoxidation