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ChemInform Abstract: Palladium-Mediated Cyclization on Carbohydrate Templates. Part 1. Synthesis of Enantiopure Bicyclic Compounds.

✍ Scribed by J.-F. NGUEFACK; V. BOLITT; D. SINOU

Publisher: John Wiley and Sons
Year: 2010
Weight: 32 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199728176

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✦ Synopsis

Palladium-Mediated Cyclization on Carbohydrate Templates. Part 1. Synthesis of Enantiopure Bicyclic Compounds. -It is shown that various 4-O-bromoalkenyl-∆2-glycopyranosides and their N-and C-analogues undergo an unexpected palladium-mediated Heck-type cyclization under Jeffery's conditions. The configuration at C-4 is found to be crucial for this process. Thus, the threo derivatives (VI) lead to formation of the tetrahydrofuran (VII). In the presence of HCOONa as hydride source, the bicyclic alkylpalladium intermediate can be trapped giving a bicyclic 2-deoxyglucal such as ( III). -(NGUEFACK,

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