Synthesis of a fluorinated Ezetimibe analogue

A facile and efficient synthesis of a fluorinated Ezetimibe analogue was achieved by radical allylation, Wacker oxidation, and nucleophilic arylation of [small alpha]-bromo-[small alpha]-fluoro-[small beta]-lactam

The synthesis of an α-fluoro-β-lactam-containing Ezetimibe analogue was accomplished starting from α-bromo-α-fluoro-β-lactam which was readily prepared from ethyl dibromofluoroacetate. A facile and efficient method for the introduction of the C3 alkyl side chain was realized via radical allylation. The diastereoselective allylation of α-bromo-α-fluoro-β-lactam was successfully applied to construct the relative configuration of the β-lactam nucleus between C3 and C4. Further modification of the allyl side chain gave the 3′-(4-fluorophenyl)-3′-hydroxypropyl group through Wacker oxidation and nucleophilic arylation.

http://pubs.rsc.org/en/Content/ArticleLanding/2015/NJ/C5NJ01969A?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FNJ+%28RSC+-+New+J.+Chem.+latest+articles%29#!divAbstract