Formal enantioselective synthesis of tacamonine starting from asymmetrized2-substituted propane-1,3-diols

2-Substituted propanediols monoacetates, derived from enzymatic asymmetriza tion of the corresponding diols, have been obtained in high yields and enan tiomeric excesses by using lipases and vinyl acetate as both solvent and ac ylating agent. These chiral building blocks have been transformed into the advanced intermediate 3, useful for the enantioselective synthesis of tacam ane alkaloids. (C) 1999 Elsevier Science Ltd. All rights reserved.