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Synthetic and novel biocatalytic resolution studies on (+/-)-5/6/7-acetoxy-4-aryl-3,4-dihydrocoumarins.
- Source :
-
Bioorganic & medicinal chemistry [Bioorg Med Chem] 2003 Feb 20; Vol. 11 (4), pp. 529-38. - Publication Year :
- 2003
-
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.
- Subjects :
- Animals
Candida enzymology
Catalysis
Chromatography, Thin Layer
Coumarins chemistry
Dealkylation
Dioxanes chemical synthesis
Magnetic Resonance Spectroscopy
Pancrelipase metabolism
Spectrophotometry, Ultraviolet
Spectroscopy, Fourier Transform Infrared
Stereoisomerism
Swine
Coumarins chemical synthesis
Lipase metabolism
Subjects
Details
- Language :
- English
- ISSN :
- 0968-0896
- Volume :
- 11
- Issue :
- 4
- Database :
- MEDLINE
- Journal :
- Bioorganic & medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 12538018
- Full Text :
- https://doi.org/10.1016/s0968-0896(02)00454-6