Abstract
-(+)-α-Allokainic acid ((+)- 1) has been prepared for the ester of cis-β-chloroacrylic acid and (-)-8-phenylmenthol by a sequence of four synthetic operations. The crucial step 8d→14d (Scheme 4) is a 1̃00%, diastereo- and 90% enantioselective intramolecular ene reaction proceeding at 35° on treatment of 8d with Me 2A1C1. Saponification of 14d regenerated the auxiliary chiral alcohol and yielded (+)- 1 on subsequent decarboxylation. In the analogous cyclization 11d→15d the sense of asymmetric induction (78% d.e.) was opposite as confirmed by the conversion of 15d to (-)-α-allokainic acid.
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