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.
Lebrun
Stéphane
S
Université des Sciences et Technologies de Lille 1, LCOP, Bâtiment C3(2), 59655 Villeneuve d'Ascq, France.
Couture
Axel
A
Deniau
Eric
E
Grandclaudon
Pierre
P
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