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

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 polyhy...

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Bibliographic Details
Published in:Chemistry : a European journal 2009-08, Vol.15 (32), p.7808-7821
Main Authors: Brandi, Alberto, Cardona, Francesca, Cicchi, Stefano, Cordero, Franca M., Goti, Andrea
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Catalysis
Cyclization
cycloaddition
glycosidase inhibitors
iminosugars
Indolizines - chemical synthesis
Indolizines - chemistry
Molecular Structure
Nitrogen Oxides - chemical synthesis
Nitrogen Oxides - chemistry
nitrones
Pyrrolizidine Alkaloids - chemical synthesis
Pyrrolizidine Alkaloids - chemistry
pyrrolizidines
Stereoisomerism
Structure-Activity Relationship
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Summary: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. Vast endowment: 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 (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200900707