Abstract
The absolute stereochemical assignment of SCH 71450, a selective dopamine D4 receptor antagonist, has been successfully confirmed through enantioselective epimer synthesis. An allyl substituent on the p-hydroxybenzyl group was demonstrated to be an appropriate protecting group for Noyori Ru-catalyzed asymmetric transfer hydrogenation of the imine derivative. The construction of the sugar moiety involved a β-glycosylation reaction assisted by neighboring group participation. By comparison with literature data, the absolute stereochemistry at the C-1 carbon on the tetrahydroisoquinoline core has been assigned the S configuration.
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