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ChemInform Abstract: Cyclopropanation of Nitroso Diels-Alder Cycloadducts and Application to the Synthesis of a 2′,3′-Methano Carbocyclic Nucleoside.

Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, Indiana, 46556, United States.
Tetrahedron Letters (Impact Factor: 2.38). 07/2010; 51(29):3789-3791. DOI: 10.1016/j.tetlet.2010.05.062
Source: PubMed

ABSTRACT

Treatment of nitroso Diels-Alder cycloadducts 1 with diazomethane in the presence of palladium acetate gives synthetically useful exo-6-oxa-7-azatricyclo[3.2.1.02,4]octane derivatives 7 in good to excellent yield. Using this methodology, a conformationally restricted 2',3'-methano carbocyclic nucleoside was efficiently synthesized from nitroso cycloadduct 1a in 7 steps.

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Available from: Marvin Miller, Jul 21, 2014
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