%0 Journal Article %J Journal of Organic Chemistry %D 2005 %T 1,3-Dipolar cycloaddition reaction of D-glucose-derived nitrone with allyl alcohol: synthesis of 2-hydroxy-1-deoxycastanospermine analogues %A Karanjule, Narayan S. %A Markad, Shankar D. %A Sharma, T. %A Sabharwal, Sushma G. %A Puranik, Vedavati G. %A Dhavale, Dilip D. %X

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.

%B Journal of Organic Chemistry %I AMER CHEMICAL SOC %C 1155 16TH ST, NW, WASHINGTON, DC 20036 USA %V 70 %P 1356-1363 %8 FEB %G eng %N 4 %9 Article %3

Foreign

%4

4.785

%R 10.1021/jo048176x