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From cyclopentadiene to isoxazoline-carbocyclic nucleosides: a rapid access to biological molecules through aza-Diels-Alder reactions |
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| Authors: | Paolo Quadrelli Andrea Piccanello Antonino Corsaro |
| 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, 6 I-95125-Catania, Italy |
| Abstract: | A rapid access to carbocyclic nucleosides containing a fused isoxazoline ring is proposed through the Grieco cycloaddition of cyclopentadiene to iminium salts. The prolific elaboration of the isoxazoline cycloadducts allowed preparation of the target aminols through the unmasking of the hydroxymethylene group at the C3 level of the azanorbornene structure. The heterocyclic aminols are readily converted into nucleosides via the linear construction of purine heterocycles. |
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