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

L Blackburn, H Kanno, RJK Taylor

Index: Blackburn, Leonie; Kanno, Hisashi; Taylor, Richard J. K. Tetrahedron Letters, 2003 , vol. 44, # 1 p. 115 - 118

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Citation Number: 32

Abstract

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-6E, 8Z, 11Z, 14Z- ...