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

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 α,β-unsaturated Weinreb amides. Elaboration of the resulting Weinreb amides i...

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Bibliographic Details
Published in:Tetrahedron letters 2003, Vol.44 (1), p.115-118
Main Authors: Blackburn, Leonie, Kanno, Hisashi, Taylor, Richard J.K.
Format: Article
Language:English
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Summary: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 α,β-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-6 E,8 Z,11 Z,14 Z-eicosatetraenoic acid. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)02498-X