A concise enantioselective synthesis of antimalarial febrifugine alkaloids.
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.
Ooi
H
H
Faculty of Pharmaceutical Sciences, Nagasaki University, Nagasaki 852-8521, Japan.
Urushibara
A
A
Esumi
T
T
Iwabuchi
Y
Y
Hatakeyama
S
S
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008968:Molecular Conformation; D015394:Molecular Structure; D010880:Piperidines; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D000962:Antimalarials; D007202:Indicators and Reagents; D010880:Piperidines; D011799:Quinazolines; C001207:febrifugine