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A stereo- and regio-controlled synthesis of bromothiophenyl C-nucleosides. Tandem bromination-ribosylation via halogen dance process |
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| Authors: | Corinne Peyron Didier Dubreuil Rachid Benhida |
| Institution: | a Laboratoire de Chimie des Molécules Bioactives et des Arômes UMR CNR-UNSA 6001, Institut de Chimie de Nice, Université de Nice-Sophia Antipolis, Parc Valrose, 06108 Nice Cedex 2, France b Université de Nantes, CEISAM, Chimie et Interdisciplinarité, Synthèse, Analyse, Modélisation, CNRS, UMR CNRS 6230, UFR des Sciences et des Techniques, 2, rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France |
| Abstract: | Metallation-ribosylation of 2-bromothiophene 1 when conducted at room temperature afforded the original glycosylated dibromothiophene 3b following a regiocontrolled halogen transfer-based halogen-dance process. Then, stereocontrolled reduction-cyclization of hemiacetals 3a-c allowed straightforward access to the halogenated thiophenyl-C-nucleosides 6a-c. |
| Keywords: | Halogen dance Tandem process Stereocontrolled synthesis C-nucleosides |
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