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

被引：33

作者：

Fustero, Santos ^{[1
,2
]}

Moscardo, Javier ^{[1
]}

Sanchez-Rosello, Maria ^{[2
]}

Flores, Sonia ^{[1
]}

Guerola, Marta ^{[1
]}

del Pozo, Carlos ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Spain

[2] Ctr Invest Principe Felipe, Lab Mol Organ, E-46012 Valencia, Spain

来源：

TETRAHEDRON | 2011年 / 67卷 / 38期

关键词：

Organocatalysis; Quinolizidine alkaloids; Intramolecular aza-Michael reaction; Myrtine; Lupinine; Epiquinamide; AZA-MICHAEL REACTION; ASYMMETRIC-SYNTHESIS; CONCISE SYNTHESIS; INDOLIZIDINE; EPIQUINAMIDE; LUPININE; ACCESS; POISON;

D O I：

10.1016/j.tet.2011.07.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 Jorgensen catalyst I, affording the common precursor with high enantioselectivity. This compound was subsequently transformed into the three alkaloids in a highly diastereoselective manner. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：7412 / 7417

页数：6

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