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Issue 12, 2015
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Synthesis of a fluorinated Ezetimibe analogue using radical allylation of α-bromo-α-fluoro-β-lactam

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Abstract

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.

Graphical abstract: Synthesis of a fluorinated Ezetimibe analogue using radical allylation of α-bromo-α-fluoro-β-lactam

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Supplementary files

Article information


Submitted
27 Jul 2015
Accepted
15 Sep 2015
First published
17 Sep 2015

New J. Chem., 2015,39, 9325-9329
Article type
Paper
Author version available

Synthesis of a fluorinated Ezetimibe analogue using radical allylation of α-bromo-α-fluoro-β-lactam

A. Tarui, A. Tanaka, M. Ueo, K. Sato, M. Omote and A. Ando, New J. Chem., 2015, 39, 9325
DOI: 10.1039/C5NJ01969A

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