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A concise enantioselective synthesis of antimalarial febrifugine alkaloids
1Faculty of Pharmaceutical Sciences, Nagasaki University, Nagasaki 852-8521, Japan.
Organic Letters
|March 27, 2001
Abstract:
Reaction of (S)-2-(tert-butyldiphenylsilyloxy)-5-(mesyloxy)pentanal with hydroxylamine in allyl alcohol brought about simultaneous 1,3-dipolar cycloaddition of the resulting nitrone to allyl alcohol to give three diastereoisomeric adducts, from which (+)-febrifugine and (+)-isofebrifugine, potent antimalarial alkaloids, were synthesized.