Synthetic and novel biocatalytic resolution studies on (+/-)-5/6/7-acetoxy-4-aryl-3,4-dihydrocoumarins.
Bioorg Med Chem
; 11(4): 529-38, 2003 Feb 20.
Article
em En
| MEDLINE
| ID: mdl-12538018
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.
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Base de dados:
MEDLINE
Assunto principal:
Cumarínicos
/
Lipase
Limite:
Animals
Idioma:
En
Ano de publicação:
2003
Tipo de documento:
Article