Synthesis of chiral pyran derivatives from a 3-O-allylfuranose-5-aldehyde by the application of intramolecular 1,3-dipolar nitrile oxide cycloaddition
R MUKHOPADHYAY, S DATTA, P CHATTOPADHYAY, A BHATTACHARJYA, A PATRA
Published in COUNCIL SCIENTIFIC INDUSTRIAL RESEARCH
Pages: 1190 - 1193
The chiral pyranoisoxazoline 5 is formed as the exclusive product in the intramolecular 1,3-dipolar nitrile oxide cycloaddition of 4 derived from the oxime of 3-O-allylfuranose-5-aldehyde 2, and is converted to the tetrasubstituted pyran 8.