Synthetic and novel biocatalytic resolution studies on (+/-)-5/6/7-acetoxy-4-aryl-3,4-dihydrocoumarins

Eleven (+/-)-5/6/7-acetoxy-4-aryl-3,4-dihydrocoumarins have been synthesised in two steps starting from the coupling of cinnamic acid/substituted cinnamic acid with appropriate phenols, followed by acetylation in 50-83% overall yields. All hydroxy- and acetoxycoumarins were unambiguously identified...

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Bibliographic Details
Published in:Bioorganic & Medicinal Chemistry
Main Authors: Singh, Ishwar, Prasad, Ashok K., Sharma, Ajendra K., Saxena, Rajendra K., Olsen, Carl E., Cholli, Ashok L., Samuelson, Lynne A., Kumar, Jayant, Watterson, Arthur C., Parmar, Virinder S.
Format: Article in Journal/Newspaper
Language:unknown
Published: Elsevier for Pergamon 2003
Subjects:
B200 Pharmacology
Toxicology and Pharmacy
Antarc*
Antarctica
Online Access:https://eprints.lincoln.ac.uk/id/eprint/11309/
https://doi.org/10.1016/S0968-0896(02)00454-6
Description
Summary:Eleven (+/-)-5/6/7-acetoxy-4-aryl-3,4-dihydrocoumarins have been synthesised in two steps starting from the coupling of cinnamic acid/substituted cinnamic acid with appropriate phenols, followed by acetylation in 50-83% overall yields. All hydroxy- and acetoxycoumarins were unambiguously identified on the basis of their spectral data. Candida antarctica lipase-catalysed deacetylation of these racemic acetoxydihydrocoumarins in dioxane occurred with moderate enantioselectivity. This is one of the rare examples of resolution using phenolic ester moiety as a remote handle for chiral recognition by a lipase. (C) 2002 Elsevier Science Ltd. All rights reserved.

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