Isoxazoline-carbocyclic aminols for nucleoside synthesis through aza-Diels-Alder reactions |
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Authors: | Paolo Quadrelli Andrea Piccanello Bruna Bovio Pierluigi Caramella |
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Institution: | a Dipartimento di Chimica Organica, Università degli Studi di Pavia, Viale Taramelli 10, 27100—Pavia, Italy b Dipartimento di Chimica Generale, Università degli Studi di Pavia, Viale Taramelli 12, 27100—Pavia, Italy |
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Abstract: | A novel approach to useful aminols for the synthesis of carbocyclic nucleosides is reported starting from a convenient source, the 2-azanorborn-5-enes. These are readily available through the Grieco cycloaddition of cyclopentadiene with iminium salts and are reactive dipolarophiles toward nitrile oxides. 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. |
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