(Z)-5-(4-Fluorophenyl)pent-4-enoic Acid: A Precursor for Convenient and Efficient Synthesis of the Antihypercholesterolemia Agent Ezetimibe

A convenient and efficient total synthesis of ezetimibe, an intestinal cholesterol absorption inhibitor and useful anticholesteremic agent, is described. Based on (Z)-5-(4-fluorophenyl)pent-4-enoic acid as a starting compound, and taking the synthesis through further Z-configured intermediates, the...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 20; pp. 3433 - 3438
Main Authors Sova, Matej, Mravljak, Janez, Kovac, Andreja, Pecar, Slavko, Casar, Zdenko, Gobec, Stanislav
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.10.2010
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Wittig reaction
azetidinone
OXIDATION
asymmetric synthesis
PRIMARY HYPERCHOLESTEROLEMIA
OLEFINS
cholesterol absorption inhibitor
(Z)-5-(4-fluorophenyl)pent-4-enoic acid
CHOLESTEROL ABSORPTION INHIBITORS
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Summary:A convenient and efficient total synthesis of ezetimibe, an intestinal cholesterol absorption inhibitor and useful anticholesteremic agent, is described. Based on (Z)-5-(4-fluorophenyl)pent-4-enoic acid as a starting compound, and taking the synthesis through further Z-configured intermediates, the total yield is remarkably increased, compared with the use of the corresponding E-configured starting substances or intermediates.
ISSN:0039-7881
DOI:10.1055/s-0030-1258193