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A new and effective route to (+/-)-botryodiplodin and (+/-)-epi-botryodiplodin acetates using a halogen atom transfer Ueno-Stork cyclization

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Published copy (DOI)

Author(s)

  • Laurent De Buyck
  • Cristina Forzato
  • Franco Ghelfi
  • Adele Mucci
  • Patrizia Nitti
  • Ugo M. Pagnoni
  • Andrew F. Parsons
  • Giuliana Pitacco
  • Fabrizio Roncaglia

Department/unit(s)

Publication details

JournalTetrahedron Letters
DatePublished - 30 Oct 2006
Issue number44
Volume47
Number of pages4
Pages (from-to)7759-7762
Original languageEnglish

Abstract

(+/-)-Botryodiplodin and (+/-)-epi-botryodiplodin acetates were prepared in good yields following a practical four step route. The method, for the construction of the strategic tetrahydrofuran ring, hinged on an unprecedented halogen atom transfer Ueno-Stork cyclization of an O-allyl alpha,alpha-dihalohemiacetal acetate, catalyzed by the redox complex CuCl/N,N,N ',N '',N ''-pentamethyldiethylenetriamine. (c) 2006 Elsevier Ltd. All rights reserved.

    Research areas

  • halocompounds, acetals, radical reactions, cyclization, Ueno-Stork, TRANSFER RADICAL CYCLIZATIONS, CHAETOMELLIC ANHYDRIDE-A, FUNCTIONAL REARRANGEMENT, PENICILLIUM-STIPITATUM, CLAISEN REARRANGEMENT, EFFICIENT ROUTE, BOTRYODIPLODIN, (-)-BOTRYODIPLODIN, STEREOCHEMISTRY, ROQUEFORTI

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