TY - JOUR
T1 - Enantioselective entry into benzoxabicyclo[2.2.1]heptyl systems via enzymatic desymmetrization
T2 - Toward chiral building blocks for lignan synthesis
AU - Berkowitz, David B.
AU - Maeng, Jun Ho
PY - 1996/6
Y1 - 1996/6
N2 - The meso diacetate, 9, available in seven steps from piperonal, is efficiently desymmetrized with preferential cleavage of the R-arm-acetate under catalysis by porcine pancreatic lipase in 10% DMSO-phosphate buffer, pH 8. The resulting monoacetate 12, a potentially useful chiral building block for the synthesis of derivatives of the Podophyllum lignans, is obtained in good chemical yield (66-83%) and in high optical yield (95% ee) on a multigram scale.
AB - The meso diacetate, 9, available in seven steps from piperonal, is efficiently desymmetrized with preferential cleavage of the R-arm-acetate under catalysis by porcine pancreatic lipase in 10% DMSO-phosphate buffer, pH 8. The resulting monoacetate 12, a potentially useful chiral building block for the synthesis of derivatives of the Podophyllum lignans, is obtained in good chemical yield (66-83%) and in high optical yield (95% ee) on a multigram scale.
UR - http://www.scopus.com/inward/record.url?scp=0030012941&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0030012941&partnerID=8YFLogxK
U2 - 10.1016/0957-4166(96)00185-1
DO - 10.1016/0957-4166(96)00185-1
M3 - Article
AN - SCOPUS:0030012941
SN - 0957-4166
VL - 7
SP - 1577
EP - 1580
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 6
ER -