01482nas a2200205 4500008004100000022001400041245014400055210006900199260007100268300001400339490000700353520064900360100002701009700002401036700001501060700002601075700002601101700002301127856012601150 2005 eng d a0022-326300a1,3-Dipolar cycloaddition reaction of D-glucose-derived nitrone with allyl alcohol: synthesis of 2-hydroxy-1-deoxycastanospermine analogues0 a13Dipolar cycloaddition reaction of Dglucosederived nitrone with a1155 16TH ST, NW, WASHINGTON, DC 20036 USAbAMER CHEMICAL SOCcFEB a1356-13630 v703 a
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.
1 aKaranjule, Narayan, S.1 aMarkad, Shankar, D.1 aSharma, T.1 aSabharwal, Sushma, G.1 aPuranik, Vedavati, G.1 aDhavale, Dilip, D. uhttp://library.ncl.res.in/content/13-dipolar-cycloaddition-reaction-d-glucose-derived-nitrone-allyl-alcohol-synthesis-2-0