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CC BY-NC-ND 4.0 · SynOpen 2021; 05(02): 145-151
DOI: 10.1055/a-1523-6428
DOI: 10.1055/a-1523-6428
paper
Enantiodivergent Synthesis of Halofuginone by Candida antarctica Lipase B (CAL-B)-Catalyzed Kinetic Resolution in Cyclopentyl Methyl Ether (CPME)
This research was supported by Huvepharma® Italia and by the University of Florence.
Abstract
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1523-6428.
- Supporting Information
Publication History
Received: 04 May 2021
Accepted after revision: 14 May 2021
Accepted Manuscript online:
07 June 2021
Article published online:
17 June 2021
© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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For a review, see:
See also:
LogP is well known to influence enzymatic activity. See, for example: