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: De Marchi E., Arnodo D., Maffeis E., Scarpi D., Prandi C., Occhiato E. G.
Other Authors: Occhiato E.G.
Format: Article in Journal/Newspaper
Language:English
Published: 2021
Subjects:
biocatalysi
halofuginone
kinetic resolution
lipase
Antarc*
Antarctica
Online Access:http://hdl.handle.net/2318/1862069
https://doi.org/10.1055/a-1523-6428
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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