title: Enantioselective route from carbohydrates to cyclooctane polyols.
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.
authors.affiliation: Evans Chemical Laboratories, Ohio State University, Columbus, OH 43210, USA. paquette.1@osu.edu
authors.forename: Leo A
authors.initials: LA
authors.lastname: Paquette
authors.forename: Yunlong
authors.initials: Y
authors.lastname: Zhang
mesh_terms: D001089:Arabinose / Q000737:chemistry; D001894:Borohydrides; D002241:Carbohydrates / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009942:Organometallic Compounds / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*; D013237:Stereoisomerism; D015040:Zirconium / Q000737:chemistry
chemical_list: D001894:Borohydrides; D002241:Carbohydrates; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D011108:Polymers; C024617:polyol; C023398:Zirconocene dichloride; C025364:sodium borohydride; D001089:Arabinose; D015040:Zirconium; D005947:Glucose