Synthetic and novel biocatalytic resolution studies on (+/-)-5/6/7-acetoxy-4-aryl-3,4-dihydrocoumarins.
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.
Singh
Ishwar
I
Bioorganic Laboratory, Department of Chemistry, University of Delhi, -110 007, Delhi, India.
Prasad
Ashok K
AK
Sharma
Ajendra K
AK
Saxena
Rajendra K
RK
Olsen
Carl E
CE
Cholli
Ashok L
AL
Samuelson
Lynne A
LA
Kumar
Jayant
J
Watterson
Arthur C
AC
Parmar
Virinder S
VS
D000818:Animals; D002175:Candida / Q000201:enzymology; D002384:Catalysis; D002855:Chromatography, Thin Layer; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D003640:Dealkylation; D004146:Dioxanes / Q000138:chemical synthesis; D008049:Lipase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D020799:Pancrelipase / Q000378:metabolism; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D013552:Swine
D003374:Coumarins; D004146:Dioxanes; D020799:Pancrelipase; D008049:Lipase