Article

Stereocontrolled cyclic nitrone cycloaddition strategy for the synthesis of pyrrolizidine and indolizidine alkaloids.

Università 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.
Chemistry (impact factor: 5.93). 08/2009; 15(32):7808-21. DOI:10.1002/chem.200900707 pp.7808-21
Source: PubMed

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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Keywords

assorted biological activity
 
iminosugars
 
isoxazolidine adducts
 
numerous stereogenic centers decorating
 
polyhydroxylated indolizidines
 
polyhydroxylated pyrroline-N-oxides
 
simple transformations
 
stereoselective 1,3-dipolar cycloaddition
 
straightforward manner