1,3-Dipolar cycloaddition reaction of D-glucose-derived nitrone with allyl alcohol: synthesis of 2-hydroxy-1-deoxycastanospermine analogues |
| |
Authors: | Karanjule Narayan S Markad Shankar D Sharma Tarun Sabharwal Sushma G Puranik Vedavati G Dhavale Dilip D |
| |
Affiliation: | Department of Chemistry, Garware Research Centre, University of Pune, Pune-411 007, India. |
| |
Abstract: | [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. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|