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

✍ Scribed by Leonie Blackburn; Hisashi Kanno; Richard J.K. Taylor

• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 313 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)02498-x

✦ Synopsis

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 a,b-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.