Asymmetric Syntheses of Pharmaceutically Interesting Piperidines

Alkyl-3-hydroxyl piperidine is a structural unit found in numerous bioactive natural products, drugs and drug candidates. For example, (+)-L-733 060 (1)1 and (+)-CP-99, 994 (2)2 are selective and potent neurokinin substance P receptor antagonists, which have been shown to possess potent antiemetic activity; febrifugine (3)3 and isofebrifugine (4)3 are well-known candidates of antimalarial agents isolated from Chinese medicinal plants Dichroa febrifuga. The important bioactivities, common str…

Asymmetric Syntheses of Pharmaceutically Interesting Piperidines

2-Alkyl-3-hydroxyl piperidine is a structural unit found in numerous bioactive natural products, drugs and drug candidates. For example, (+)-L-733 060 (1)1 and (+)-CP-99, 994 (2)2 are selective and potent neurokinin substance P receptor antagonists, which have been shown to possess potent antiemetic activity; febrifugine (3)3 and isofebrifugine (4)3 are well-known candidates of antimalarial agents isolated from Chinese medicinal plants Dichroa febrifuga. The important bioactivities, common structural features and also stereochemistry and substituents diversity associated with these piperidines have stimulated the development of 3-piperidinol synthon-based versatile approaches. We now wish to communicate on the development of a new 3-piperidinol synthon A and its application in the asymmetric synthesis of (+)-L-733 060 (1), (+)-CP-99, 994 (2),febrifugine (3) and isofebrifugine (4).