title: Synthesis of chiral cyclohexanes and carbasugars by 6-exo-dig radical cyclisation reactions.
abstract: Treatment of 5-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribose with lithium acetylides gave mixtures of syn- and anti-alkynols 2a-2c which were separated following protection as methoxymethyl ethers. These were converted to the corresponding iodides which underwent 6-exo-dig radical cyclisation to afford chiral cyclohexanes and carbasugars. Oxidation of the primary alcohols 6a-b gave the corresponding aldehydes which on treatment with Grignard reagents afforded a mixture of alcohols. The corresponding iodides underwent similar 6-exo-dig cyclisation to give fully functionalised cyclohexanes.
authors.affiliation: Department of Chemistry, University of Sunderland, Sunderland, SR1 3SD, UK. Rajeev.Shrivastava@edgehill.ac.uk
authors.forename: Rajeev K
authors.initials: RK
authors.lastname: Shrivastava
authors.forename: Elise
authors.initials: E
authors.lastname: Maudru
authors.forename: Gurdial
authors.initials: G
authors.lastname: Singh
authors.forename: Richard H
authors.initials: RH
authors.lastname: Wightman
authors.forename: Keith M
authors.initials: KM
authors.lastname: Morgan