- From common carbohydrates to enantiopure cyclooctane polyols and glycomimetics via deoxygenative zirconocene ring contraction.
From common carbohydrates to enantiopure cyclooctane polyols and glycomimetics via deoxygenative zirconocene ring contraction.
The Journal of organic chemistry (2006-06-06)
Leo A Paquette, Yunlong Zhang
PMID16749762
ABSTRACT
D-Arabinose and D-glucose are transformed into the identical vinyl furanoside, whose role is to serve as the precursor to enantiopure cyclooctadienone 6. The key steps of this relay involve a zirconocene-promoted ring contraction and [3,3] sigmatropic rearrangement of an enynol. Subsequently defined are convenient synthetic routes to several cyclooctane-1,2,3-triols, 1,2,3,4,5-pentaols, and structurally related glycomimetics.
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