Enantiodivergent Synthesis of Halofuginone by Candida antarctica Lipase B (CAL-B)-Catalyzed Kinetic Resolution in Cyclopentyl Methyl Ether (CPME)

The synthesis of both enantiomers of a key intermediate in the synthesis of halofuginone was accomplished by a Candida antarctica lipase B (CAL-B)-catalyzed kinetic resolution of the corresponding racemate. When the resolution was carried out in the versatile solvent cyclopentyl methyl ether (CPME)...

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Bibliographic Details
Published in:SynOpen
Main Authors: Elisa De Marchi, Davide Arnodo, Elia Maffeis, Dina Scarpi, Cristina Prandi, Ernesto G. Occhiato
Format: Article in Journal/Newspaper
Language:English
Published: Georg Thieme Verlag KG 2021
Subjects:
biocatalysis
lipase
kinetic resolution
halofuginone
Chemistry
QD1-999
Antarc*
Antarctica
Online Access:https://doi.org/10.1055/a-1523-6428
https://doaj.org/article/29ab8c99137548199062a896a8204827
Description
Summary:The synthesis of both enantiomers of a key intermediate in the synthesis of halofuginone was accomplished by a Candida antarctica lipase B (CAL-B)-catalyzed kinetic resolution of the corresponding racemate. When the resolution was carried out in the versatile solvent cyclopentyl methyl ether (CPME) using p-chlorophenylbutyrate (PCPB) as the acylating reagent, the highest enantiomeric ratio (E) values were measured, and highly enantioenriched (95% ee) compounds could be obtained in a single iteration. As an example, one of the two enantiomers was used as a starting material to prepare (+)-halofuginone in a three-step procedure.

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