TY - JOUR T1 - 1,3-Dipolar cycloaddition reaction of D-glucose-derived nitrone with allyl alcohol: synthesis of 2-hydroxy-1-deoxycastanospermine analogues JF - Journal of Organic Chemistry Y1 - 2005 A1 - Karanjule, Narayan S. A1 - Markad, Shankar D. A1 - Sharma, T. A1 - Sabharwal, Sushma G. A1 - Puranik, Vedavati G. A1 - Dhavale, Dilip D. AB -

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.

PB - AMER CHEMICAL SOC CY - 1155 16TH ST, NW, WASHINGTON, DC 20036 USA VL - 70 IS - 4 U3 -

Foreign

U4 -

4.785

ER -