Journal of Organic Chemistry p. 1765 - 1771 (1987)
Update date:2022-07-29
Topics: Yield Total synthesis Reaction Conditions Chiral molecule (-)-Chorismic Acid (-)-Shikimic Acid
Pawlak, John L.
Berchtold, Glenn A.
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.
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