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

Singh, Ishwar and Prasad, Ashok K. and Sharma, Ajendra K. and Saxena, Rajendra K. and Olsen, Carl E. and Cholli, Ashok L. and Samuelson, Lynne A. and Kumar, Jayant and Watterson, Arthur C. and Parmar, Virinder S. (2003) Synthetic and novel biocatalytic resolution studies on (+/-)-5/6/7-acetoxy-4-aryl-3,4-dihydrocoumarins. Bioorganic and Medicinal Chemistry, 11 (4). pp. 529-538. ISSN 0968-0896

Full content URL: http://dx.doi.org/10.1016/S0968-0896(02)00454-6

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Item Type:Article
Item Status:Live Archive

Abstract

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.

Keywords:Pharmacy
Subjects:B Subjects allied to Medicine > B200 Pharmacology, Toxicology and Pharmacy
Divisions:College of Science > School of Pharmacy
ID Code:11309
Deposited On:24 Jul 2013 09:04

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