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. 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 |
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| 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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