A Straightforward Synthesis of Isoxazoline-Based Carbocyclic Nucleosides from 1,3-Cyclohexadiene through Nitrosocarbonyl Chemistry

3-Benzoyl-2-oxa-3-azabicyclo[2.2.2]oct-5-ene undergoes cycloaddition with benzonitrile oxide to afford a mixture of syn and anti regioisomeric cycloadducts. The anti cycloadducts were easily elaborated to stereodefined isoxazoline-based carbocyclic aminols that serve as synthons for the linear construction of purine nucleosides. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)