Stereocontrolled Cyclic Nitrone Cycloaddition Strategy for the Synthesis of Pyrrolizidine and Indolizidine Alkaloids

被引：243

作者：

Brandi, Alberto ^{[1
]}

Cardona, Francesca ^{[1
]}

Cicchi, Stefano ^{[1
]}

Cordero, Franca M. ^{[1
]}

Goti, Andrea ^{[1
]}

机构：

[1] Univ Florence, Dipartmento Chim Organ U Schiff, Lab Progettaz Sintesi & Studio Eterocicli Biologi, Heterobiolab, I-50019 Sesto Fiorentino, FI, Italy

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 32期

关键词：

cycloaddition; glycosidase inhibitors; iminosugars; nitrones; pyrrolizidines; TUNGSTATE-CATALYZED OXIDATION; DOUBLE ASYMMETRIC INDUCTION; 1,3-DIPOLAR CYCLOADDITION; GLYCOSIDASE INHIBITORS; HYDROGEN-PEROXIDE; STEREOSELECTIVE-SYNTHESIS; NUCLEOPHILIC ADDITIONS; SECONDARY-AMINES; HYDROXYLATED PYRROLIZIDINES; ENANTIOSELECTIVE SYNTHESIS;

D O I：

10.1002/chem.200900707

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of polyhydroxylated indolizidines and pyrrolizidines belonging to the class of imino-sugars, endowed with a vast and assorted biological activity, can be achieved in a straightforward manner by a general strategy consisting of a highly stereoselective 1,3-dipolar cycloaddition of polyhydroxylated pyrroline-N-oxides followed by simple transformations of the isoxazolidine adducts. The strategy allows the complete control of the relative and absolute stereochemistry of the numerous stereogenic centers decorating these compounds.

引用

页码：7808 / 7821

页数：14

共 141 条

[1] Lipase-catalyzed domino kinetic resolution of α-hydroxynitrones/intramolecular 1,3-dipolar cycloaddition:: a concise asymmetric total synthesis of (-)-rosmarinecine [J].