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

Authors :
Singh I
Prasad AK
Sharma AK
Saxena RK
Olsen CE
Cholli AL
Samuelson LA
Kumar J
Watterson AC
Parmar VS
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.

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