Lipase-catalysed regio- and enantioselective deacetylation of 2,4-diacetoxyphenyl alkyl ketones.
Porcine pancreatic lipase in tetrahydrofuran catalyses the deacetylation of 2,4-diacetoxyphenyl alkyl ketones in a highly regioselective fashion. The strategy of regioselective deacetylation of diacetoxyphenyl alkyl ketones has also resulted in the enantiomeric resolution of a racemic diacetoxyphenyl alkyl ketone, i.e. (+/-)-2,4-diacetoxyphenyl (1-ethyl)pentyl ketone, a precursor for the synthesis of an antifungal coumarin, 7-acetoxy-4-(1-ethyl)pentyl-3-phenyl-2H-1-benzopyran-2-one.
Prasad
A K
AK
Department of Chemistry, University of Delhi, India.
Pati
H N
HN
Azim
A
A
Trikha
S
S
Poonam
D000107:Acetylation; D000818:Animals; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D008049:Lipase / Q000737:chemistry*; D010179:Pancreas / Q000201:enzymology; D013057:Spectrum Analysis; D013237:Stereoisomerism; D013552:Swine
D007659:Ketones; D008049:Lipase