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From cyclopentadiene to isoxazoline-carbocyclic nucleosides: a rapid access to biological molecules through nitrosocarbonyl chemistry |
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| Authors: | Paolo Quadrelli Roberto Scrocchi Antonio Rescifina |
| Institution: | a Dipartimento di Chimica Organica, Università degli Studi di Pavia, Viale Taramelli, 10 I-27100 Pavia, Italy b Dipartimento di Scienze Chimiche, Università degli Studi di Catania, Viale A. Doria, 8 I-95125 Catania, Italy c Dipartimento Farmaco-Chimico, Università degli Studi di Messina, Viale S.S. Annunziata I-98168 Messina, Italy |
| 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. |
| Keywords: | Carbocyclic nucleosides Nitrosocarbonyls Nitrile oxides Cycloadditions |
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