The synthesis and X-ray crystal structure of a cyclopentaannulated sugar; the first example of an intramolecular aldol cyclopentaannulation in carbohydrate chemistry

Abstract

A 1,4-dicarbonyl compound 5 has been constructed by a sequence involving opening of a protected glucose epoxide with allyl magnesium chloride, alkylation and Wacker oxidation; the 1,4-dicarbonyl compound readily undergoes cyclisalion under basic conditions to produce a Cyclopentaannulated sugar derivative 6, whose structure was confirmed by X-ray crystallography.