ChemInform Abstract: Fragmentation of Carbohydrate Anomeric Alkoxy Radicals. A New General Method for the Synthesis of Alduronic Acid Lactones.

✍ Scribed by C. G. FRANCISCO; C. GONZALEZ MARTIN; E. SUAREZ

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 42 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199832266

✦ Synopsis

Fragmentation of Carbohydrate Anomeric Alkoxy Radicals. A New General Method for the Synthesis of Alduronic Acid Lactones. -In the presence of Ph-I(O-Ac) 2 /I 2 as well as diphenylhydroxyselenium acetate/I 2 /visible light carbohydrates of type (I), (III), and (V) smoothly undergo tandem β-fragmentation-intramolecular cyclization to title lactones, which are useful synthetic synthons. Alternatively, an intermolecular reaction takes place when the carboxyl group is lactonized [cf. (VII)→(VIII)]. -(FRANCISCO, C. G.;