Enantiodivergent Synthesis of Halofuginone by Candida Antarctica Lipase B (CAL-B)-catalyzed Kinetic Resolution in Cyclopentyl Methyl Ether (CPME)
Keyword(s):
Lipase B
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The synthesis of both enantiomers of a key intermediate in the synthesis of halofuginone was accomplished by Candida antarctica lipase B-catalyzed kinetic resolution of the corresponding racemate. When the resolution was carried out in the versatile and eco-friendly solvent cyclopentyl methyl ether (CPME) using PCPB (p-chlorophenylbutyrate) 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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2018 ◽
Vol 110
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pp. 8-13
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2012 ◽
Vol 23
(3-4)
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pp. 230-236
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2001 ◽
Vol 11
(4-6)
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pp. 1025-1028
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1995 ◽
Vol 6
(12)
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pp. 3023-3030
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2014 ◽
Vol 80
(1)
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pp. 521-527
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2004 ◽
Vol 26
(4)
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pp. 301-306
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