Organocatalytic enantioselective synthesis of quinolizidine alkaloids (+)-myrtine, (−)-lupinine, and (+)-epiepiquinamide |
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| Authors: | Santos Fustero Javier MoscardóMaría Sánchez-Roselló Sonia FloresMarta Guerola Carlos del Pozo |
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| Institution: | a Departamento de Química Orgánica, Universidad de Valencia, E-46100 Burjassot, Spain
b Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, E-46012 Valencia, Spain |
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| 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. |
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| Keywords: | Organocatalysis Quinolizidine alkaloids Intramolecular aza-Michael reaction Myrtine Lupinine Epiquinamide |
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