From cyclic polyenes to carbohydrates: synthesis of the hexose sugar β-allose and its 2C-branched homologue from cyclooctatetraene

Abstract

In an unconventional but interesting synthetic enterprise, the commercially available hydrocarbon cyclooctatetraene (COT) has been elaborated to the rare hexose sugar (DL)-β-allose and its 2C-branched analogue. The synthetic sequence delineated here is notable for its high regio- and stereoselectivity and is flexible enough to enable access to polyoxygenated systems, hexose sugars, and their siblings from a cyclic polyene precursor.