title: Concise synthesis of aryl-C-nucleosides by Friedel-Crafts alkylation.
abstract: A fast and simplified synthesis of 1',2'-dideoxy-1'-pyrenyl-riboside and several other C-nucleosides is shown. Shelf-stable 1-O-methyl-3,5-di-O-toluoyl-2-deoxyribose is demonstrated to serve as a versatile glycosyl donor in Lewis acid promoted Friedel-Crafts alkylations of unsubstituted pyrene and other inexpensive arenes such as fluorene and methylnaphthalene. The reaction conditions favour the formation of beta-configurated C-nucleosides which renders additional epimerisation steps unnecessary. As a result, protected beta-aryl-C-nucleosides are available directly from non-substituted arenes in three steps overall.
authors.affiliation: Humboldt-Universität zu Berlin, Institut für Chemie, Brook-Taylor Str. 2, D-12489, Berlin, Germany.
authors.forename: Sven
authors.initials: S
authors.lastname: Hainke
authors.forename: Sebastian
authors.initials: S
authors.lastname: Arndt
authors.forename: Oliver
authors.initials: O
authors.lastname: Seitz
mesh_terms: D000478:Alkylation; D006841:Hydrocarbons, Aromatic; D009705:Nucleosides / Q000138:chemical synthesis*
chemical_list: D006841:Hydrocarbons, Aromatic; D009705:Nucleosides