Concise synthesis of aryl-C-nucleosides by Friedel-Crafts alkylation.
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.
Hainke
Sven
S
Humboldt-Universität zu Berlin, Institut für Chemie, Brook-Taylor Str. 2, D-12489, Berlin, Germany.
Arndt
Sebastian
S
Seitz
Oliver
O
D000478:Alkylation; D006841:Hydrocarbons, Aromatic; D009705:Nucleosides / Q000138:chemical synthesis*
D006841:Hydrocarbons, Aromatic; D009705:Nucleosides