@article { ISI:000227075600029,
	title = {1,3-Dipolar cycloaddition reaction of D-glucose-derived nitrone with allyl alcohol: synthesis of 2-hydroxy-1-deoxycastanospermine analogues},
	journal = {Journal of Organic Chemistry},
	volume = {70},
	number = {4},
	year = {2005},
	month = {FEB},
	pages = {1356-1363},
	publisher = {AMER CHEMICAL SOC},
	type = {Article},
	address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA},
	abstract = {<p>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.</p>},
	issn = {0022-3263},
	doi = {10.1021/jo048176x},
	author = {Karanjule, Narayan S. and Markad, Shankar D. and Sharma, T. and Sabharwal, Sushma G. and Puranik, Vedavati G. and Dhavale, Dilip D.}
}
