In situ alcohol oxidation-Wittig reactions using N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide: application to the synthesis of a novel analogue of 5-oxo-eicosatetraenoic acid

L Blackburn, H Kanno, R J K Taylor

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Benzylic, allylic, propargylic and unactivated alcohols can be oxidised with activated manganese dioxide in the presence of N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide to generate directly the corresponding alpha,beta-unsaturated Weinreb amides. Elaboration of the resulting Weinreb amides is also described, in particular as part of a new route to analogues of the arachidonic acid metabolite 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)115-118
Number of pages4
JournalTetrahedron Letters
Issue number1
Publication statusPublished - 1 Jan 2003


  • 5-OXO-ETE

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