1,3-Dipolar Cycloaddition Reaction of d-Glucose-Derived Nitrone with Allyl Alcohol:  Synthesis of 2-Hydroxy-1-deoxycastanospermine Analogues

The synthesis and evaluation of glycosidase inhibitory activity of polyhydroxylated indolizidine alkaloids namely 2-hydroxy-1-deoxycastanospermine 3a,b and 2-hydroxy-1-deoxy-8a-epi-castanospermine 3c,d is reported. The key step involves the intermolecular 1,3-dipolar cycloaddition of allyl alcohol t...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-02, Vol.70 (4), p.1356-1363
Main Authors: Karanjule, Narayan S, Markad, Shankar D, Sharma, Tarun, Sabharwal, Sushma G, Puranik, Vedavati G, Dhavale, Dilip D
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Glucose - chemistry
Glycoside Hydrolases - antagonists & inhibitors
Glycoside Hydrolases - metabolism
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Indolizines
Inhibitory Concentration 50
Molecular Conformation
Molecular Structure
Nitrogen Oxides - chemistry
Organic chemistry
Preparations and properties
Propanols - chemistry
Stereoisomerism
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Summary:The synthesis and evaluation of glycosidase inhibitory activity of polyhydroxylated indolizidine alkaloids namely 2-hydroxy-1-deoxycastanospermine 3a,b and 2-hydroxy-1-deoxy-8a-epi-castanospermine 3c,d is reported. The key step involves the intermolecular 1,3-dipolar cycloaddition of allyl alcohol to d-glucose-derived nitrone 4, followed by tosylation, that afforded four diastereomeric sugar-substituted isoxazolidines 5a−d with the desired regioselectivity. The one-pot conversion of 5a−d to pyrrolidines 8a−d by hydrogenolysis, removal of 1,2-acetonoide functionality, and hydrogenation afforded corresponding target molecules 3a−d.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo048176x