Stereoselective asymmetric synthesis of (+)-sedamine and (+)-allosedamine.
A convenient method for the generation of (+)-sedamine and (+)-allosedamine in high optical purity has been elaborated. The key steps are the highly stereoselective 1,2-nucleophilic addition to SAMP hydrazones allowing the installation of the stereogenic center at C2 and ring closing metathesis.
Université des Sciences et Technologies de Lille 1, LCOP, Bâtiment C3(2), 59655 Villeneuve d'Ascq, France.
Stéphane
S
Lebrun
Axel
A
Couture
Eric
E
Deniau
Pierre
P
Grandclaudon
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry; D006835:Hydrazones / Q000737:chemistry*; D015394:Molecular Structure; D010663:Phenylmercury Compounds; D010721:Phosphinic Acids / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011188:Potassium / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D004852:Epoxy Compounds; D006835:Hydrazones; D010663:Phenylmercury Compounds; D010721:Phosphinic Acids; D010880:Piperidines; C459239:sedamine; C036235:4-(4-sulfophenylazo)-2-mercuriphenol; D011188:Potassium