Stereoselective Synthesis of Ezetimibe via Cross-Metathesis of Homoallylalcohols and α-Methylidene-β-Lactams.

Authors :: Humpl M
Tauchman J
Topolovčan N
Kretschmer J
Hessler F
Císařová I
Kotora M
Veselý J
Source :: The Journal of organic chemistry [J Org Chem] 2016 Sep 02; Vol. 81 (17), pp. 7692-9. Date of Electronic Publication: 2016 Aug 18.
Publication Year :: 2016
Abstract: Ru-catalyzed cross-metathesis (CM) reaction between β-arylated α-methylidene-β-lactams and terminal olefins was developed. The CM reaction is effectively catalyzed with Hoveyda-Grubbs second-generation catalyst affording corresponding α-alkylidene-β-aryl-β-lactams in good isolated yields (41-83%) with exclusive Z-selectivity. The developed protocol was successfully applied for stereoselective preparation of Ezetimibe, the commercial cholesterol absorption inhibitor.

Subjects :: Anticholesteremic Agents chemistry
Catalysis
Cyclization
Ezetimibe chemistry
Ruthenium chemistry
Spectrum Analysis methods
Stereoisomerism
Anticholesteremic Agents chemical synthesis
Ezetimibe chemical synthesis
Propanols chemistry
beta-Lactams chemistry

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