Organic Letters 2005-02-03

Enantioselective route from carbohydrates to cyclooctane polyols.

Leo A Paquette, Yunlong Zhang

Index: Org. Lett. 7(3) , 511-3, (2005)

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Abstract

[reaction: see text] A synthetic route to select cyclooctane-1,2,3-triols and 1,2,3,4,5-pentaols has been defined. The starting materials are d-glucose or d-arabinose, and the key steps consist of a zirconocene-promoted ring contraction, a [3,3] sigmatropic rearrangement, and more extended functionalization of the resulting cyclooctadienone.