Catalytic asymmetric synthesis of febrifugine and isofebrifugine

Article abstract of DOI:10.1016/S0040-4039(99)00142-2

Antimalarial alkaloids, febrifugine (1) and isofebrifugine (2), were synthesized from simple achiral starting materials using tin(II)-catalyzed catalytic asymmetric aldol reaction and lanthanide-catalyzed aqueous three- component reaction as the key steps. These unambigous total syntheses revealed that the absolute configurations of febrifugine and isofebrifugine were not (2'S, 3'R) and (2'R, 3'R) as reported previously but (2'R, 3'S) and (2'S, 3'S), respectively.