Abstract
Porcine pancreatic lipase pre-incubated with phenyl methyl ketone in THF fails to recognize the ortho- and para-acetoxy functions with respect to the nuclear carbonyl group towards deacetylation reaction on 2,4-diacetoxyphenyl methyl ketones; this result is in conformity with our hypothesis on the mechanism of action of PPL in THF. Further, four racemic 2,4-diacetoxyphenyl alkyl ketones, the precursors for the synthesis of analogs of a potent antifungal coumarin, 7-acetoxy-4-(1-ethyl)pentyl-3-phenyl-2H-1-benzopyran-2-one, have been synthesized by Nencki's reaction between resorcinol and corresponding (±)-aliphatic acid, followed by acetylation of the resulting (±)-2,4-dihydroxyphenyl alkyl ketones. Porcine pancreatic lipase has been used successfully for regio- and enantioselective deacetylation of these diacetoxyphenyl alkyl ketones in tetrahydrofuran.
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