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IJC-B Vol.46B(09) [September 2007] >

Title: Biocatalytic acylation studies on novel 3-aryl-3-hydroxymethyl-2, 3-dihydro-4H-1- benzopyran-4-ones
Authors: Kumar, Vijayendra
Rajesh Kumar
Sharma, Sunil K
Prasad, Ashok K
Cholli, Ashok L
Olsen, Carl E
Parmar, Virinder S
Keywords: Isoflavanones
Biocatalytic resolution
Acylating agents
Heptanoic anhydride
Issue Date: Sep-2007
Publisher: CSIR
Abstract: (±)-3-Aryl-3-hydroxymethyl-2,3-dihydro-4H-1- benzopyran-4-ones have been synthesized in four steps starting with the coupling of resorcinol with corresponding phenylacetic acid leading to the formation of 2,4-dihydroxyphenyl aryl ketones, which upon monomethylation/benzylation and hydroxymethylation afford (±)-hydroxymethylisoflavanones in 65-70% yields. These isoflavanones have been subjected to lipase-catalyzed acylation reactions under different conditions (for optimization) of varying solvents, enzymes and acylating agents. Candida antarctica lipase B in tetrahydrofuran using heptanoic anhydride at 90 ºC is found to be the best reaction protocol for the biocatalytic reaction.
Page(s): 1501-1510
ISSN: 0376-4699
Source:IJC-B Vol.46B(09) [September 2007]

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