Highly functionalised cyclobutanols via samarium(II) iodide-induced pinacol cyclisations of carbohydrate-derived 1,4-diketones.
D-Ribofuranose and D-arabinofuranose derivatives were converted in a few steps into their 1,4-diketone derivatives, which were pinacol cyclised under the action of SmI2 to form the corresponding chiral cyclobutanediol products. These products can potentially be applied to the synthesis of anti-viral agents, some of whose structures incorporate chiral cyclobutanediol moieties.
Williams
D Bradley G
DB
Department of Chemistry, University of Johannesburg, PO Box 524, Auckland Park, 2006, South Africa. dbgw@rau.ac.za
Caddy
Judy
J
Blann
Kevin
K
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry; D001089:Arabinose / Q000031:analogs & derivatives* / Q000737:chemistry; D000440:Butanols / Q000737:chemistry; D002240:Carbohydrate Sequence; D003500:Cyclization; D003503:Cyclobutanes / Q000138:chemical synthesis*; D007454:Iodides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008969:Molecular Sequence Data; D012266:Ribose / Q000031:analogs & derivatives / Q000737:chemistry*; D012493:Samarium / Q000737:chemistry*
D000998:Antiviral Agents; D000440:Butanols; D003503:Cyclobutanes; D007454:Iodides; D007659:Ketones; C431714:arabinofuranose; D012493:Samarium; D012266:Ribose; D001089:Arabinose; C409809:samarium diiodide