title: Synthesis of (carbo)nucleoside analogues by [3+2] annulation of aminocyclopropanes.
abstract: (Carbo)nucleoside derivatives constitute an important class of pharmaceuticals, yet there are only few convergent methods to access new analogues. Here, we report the first synthesis of thymine-, uracil-, and 5-fluorouracil-substituted diester donor-acceptor cyclopropanes and their use in the indium- and tin-catalyzed [3+2] annulations with aldehydes, ketones, and enol ethers. The obtained diester products could be easily decarboxylated and reduced to the corresponding alcohols. The method gives access to a broad range of new (carbo)nucleoside analogues in only four or five steps and will be highly useful for the synthesis of libraries of bioactive compounds.
authors: Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne (Switzerland) http://lcso.epfl.ch/
authors: Sophie
authors: S
authors: Racine
authors: Florian
authors: F
authors: de Nanteuil
authors: Eloisa
authors: E
authors: Serrano
authors: Jérôme
authors: J
authors: Waser
mesh_terms: D061565:Cycloaddition Reaction; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003521:Cyclopropanes; D009705:Nucleosides
keywords: annulation; catalysis; cyclopropanes; nucleosides; stereoselective synthesis