1,3-Dipolar cycloaddition reaction of D-glucose-derived nitrone with allyl alcohol: synthesis of 2-hydroxy-1-deoxycastanospermine analogues.
[reaction: see text] 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.
Karanjule
Narayan S
NS
Department of Chemistry, Garware Research Centre, University of Pune, Pune-411 007, India.
Markad
Shankar D
SD
Sharma
Tarun
T
Sabharwal
Sushma G
SG
Puranik
Vedavati G
VG
Dhavale
Dilip D
DD
D005947:Glucose / Q000737:chemistry*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors / Q000378:metabolism; D007212:Indolizines; D020128:Inhibitory Concentration 50; D008968:Molecular Conformation; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
C500280:2-hydroxy-1-deoxycastanospermine; D007212:Indolizines; D009589:Nitrogen Oxides; D020005:Propanols; C015388:nitrones; C006463:allyl alcohol; D006026:Glycoside Hydrolases; D005947:Glucose