Enantioselective route from carbohydrates to cyclooctane polyols.
[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.
Paquette
Leo A
LA
Evans Chemical Laboratories, Ohio State University, Columbus, OH 43210, USA. paquette.1@osu.edu
Zhang
Yunlong
Y
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
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