112835-91-3Relevant articles and documents
APPLICATION OF MICROORGANISMS AND ENZYMES TO THE SYNTHESIS OF CHIRAL CYCLOPENTANE AND BICYCLOOCTANE DERIVATIVES
Xie, Zhuo-Feng,Suemune, Hiroshi,Nakamura, Izumi,Sakai, Kiyoshi
, p. 4454 - 4459 (2007/10/02)
Optically active cyclopentane and bicyclooctane derivatives were synthesized by utilizing biochemical methods.Pseudomonas fluorescens lipase was found to be an effective enzyme for the enantioselective hydrolysis of monoacetoxy- and diacetoxycyclopentanes such as (+/-)-4a, (+/-)-5a, (+/-)-6a, and 7a.However,hydrolysis of bicyclooctane trans-acetate ((+/-)-8a) using this enzyme resulted low enantioselectivity.Optically pure (+)-8b for the synthesis of carbacyclin was obtained from (+/-)-8a by using porcine pancreatic lipase.Reduction of 3-acetyl-7-oxobicyclo-oct-2-ene with baker's yeast afforded a useful intermediate((+)-11b) for the synthesis of hirsutic acid.Keywords - enzymatic hydrolysis; enantioselective hydrolysis; bicyclo-octane; baker's yeast; carbacyclin; hirsutic acid