Stereocontrolled cyclic nitrone cycloaddition strategy for the synthesis of pyrrolizidine and indolizidine alkaloids
Alberto Brandi1, Francesca Cardona1, Stefano Cicchi1
1Università degli Studi di Firenze, Dipartimento di Chimica Organica "U. Schiff", Laboratorio di Progettazione, Sintesi e Studio di Eterocicli Biologicamenti Attivi (HeteroBioLab), Via della Lastruccia 13, 50019 Sesto Fiorentino (FI) (Italy), Fax: (+39) 0554573572.
Abstract:
The synthesis of polyhydroxylated indolizidines and pyrrolizidines belonging to the class of iminosugars, 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.
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