Tetrahedron

Organocatalytic enantioselective synthesis of quinolizidine alkaloids (+)-myrtine,(−)-lupinine, and (+)-epiepiquinamide

S Fustero, J Moscardó, M Sánchez-Roselló, S Flores…

Index: Fustero, Santos; Moscardo, Javier; Sanchez-Rosello, Maria; Flores, Sonia; Guerola, Marta; Pozo, Carlos Del Tetrahedron, 2011 ,  vol. 67,  # 38  p. 7412 - 7417

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Citation Number: 24

Abstract

The organocatalytic synthesis of quinolizidine alkaloids (+)-myrtine,(−)-lupinine, and (+)- epiepiquinamide is described. It involved, as the key step, an enantioselective intramolecular aza-Michael reaction (IMAMR) catalyzed by Jørgensen catalyst I, affording the common precursor with high enantioselectivity. This compound was subsequently transformed into the three alkaloids in a highly diastereoselective manner.