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  • Title: Synthesis of spirocyclic C-arylglycosides and -ribosides by ruthenium-catalyzed cycloaddition.
    Author: Yamamoto Y, Yamashita K, Hotta T, Hashimoto T, Kikuchi M, Nishiyama H.
    Journal: Chem Asian J; 2007 Nov 05; 2(11):1388-99. PubMed ID: 17907128.
    Abstract:
    Spirocyclic C-arylglycosides were synthesized from the appropriately protected delta-gluconolactones. Addition of lithium acetylide followed by glycosylation with 3-(trimethylsilyl)propargyl alcohol converted the delta-gluconolactones into silylated diynes. After desilylation, subsequent ruthenium-catalyzed cycloaddition of the resultant diynes with alkynes or chloroacetonitrile gave spirocyclic C-arylglycosides in good yields and selectivity. This strategy was also extended to the synthesis of spirocyclic C-arylribosides from the known gamma-ribonolactone derivative. Moreover, silver-catalyzed iodination of the sugar diynes followed by ruthenium-catalyzed cycloaddition with acetylene delivered spirocyclic C-iodophenylglycosides and -ribosides, which were subjected to palladium-catalyzed C-C bond-forming reactions and copper-catalyzed coupling with nitrogen heterocycles to lead to various derivatives.
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