Total Synthesis of (-)-Chorismic Acid and (-)-Shikimic Acid

Article abstract of DOI:10.1021/jo00385a022

A survey of the enantioselective hydrolyses of 5a-h and 6a-c with commercially available lipases and cholesterol esterases is reported.A procedure for the preparative-scale synthesis of enantiomerically pure (+)-4 and (-)-4 by the enantioselective hydrolysis of 6a or 6b with cholesterol esterase from bovine pancreas is described.Enantiomerically pure (-)-3 is prepared from either (+)-4 or (-)-4.A short total synthesis of (-)-chorismic acid (22percent) from (-)-3 and of (-)-shikimic acid (94percent) from (-)-4 is reported.