Tetrahedron

From cyclopentadiene to isoxazoline–carbocyclic nucleosides: A rapid access to biological molecules through nitrosocarbonyl chemistry

P Quadrelli, R Scrocchi, P Caramella, A Rescifina…

Index: Quadrelli, Paolo; Scrocchi, Roberto; Caramella, Pierluigi; Rescifina, Antonio; Piperno, Anna Tetrahedron, 2004 , vol. 60, # 16 p. 3643 - 3651

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Citation Number: 37

Abstract

A rapid access to carbocyclic nucleosides containing a fused isoxazoline ring is proposed starting from cyclopentadiene. The route involves an hetero Diels–Alder cycloaddition reaction of nitrosocarbonylbenzene followed by a 1, 3-dipolar cycloaddition of nitrile oxides, cleavage of the N–O tether and elaboration of the heterocyclic aminols into nucleosides via linear construction of purine and pyrimidine heterocycles.