Potent glycosidase inhibitors via hetero Diels-Alder reactions: asymmetric synthesis of 5-methyl-trihydroxypyrrolidines

✍ Scribed by A. Defoin; Th. Sifferlen; J. Streith; I. Dosbaâ; M.-J. Foglietti

• Publisher: Elsevier Science
• Year: 1997
• Tongue: English
• Weight: 186 KB
• Volume: 8
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(97)00008-6

✦ Synopsis

Some straightforward chemical transformations of oxazine diol 4, which was obtained from sorbaldehyde 2 by an asymmetric hetero Diels-Alder reaction followed by osmylation, led to the protected dihydroxypyrrolidine-aldehyde 8a and, after basic epimerisation, to 8b. Reduction of the aldehyde moiety and deprotection gave the potent glycosidase inhibitors 2,5,6-trideoxy-2,5-imino-D-altritol and D-allitol 9a and 9b. (~) 1997 Elsevier Science Ltd. All rights reserved.