The 1,3-dipolar cycloaddition of enantiopure cyclic hydroxylated nitrones and allyl nucleobases has been exploited for the preparation of a novel class of homonucleoside mimetics, where the furanose ring is replaced by a pyrrolo[1,2-b]isoxazolidine system. The nitrones were easily prepared starting from L-malic and L-tartaric acids and gave cycloadducts in a diastereoselective manner, which were deprotected to give good yields of the homo-N,O-nucleoside mimetics. The reduction of the isoxazolidine ring, a 1,3- aminoalcohol equivalent, allows easy access to other new pyrrolidine nucleoside mimetics.
Diastereoselective synthesis of a collection of new homonucleoside mimetics containing pyrrolo[1,2-b]isoxazoline and pyrrolidine rings / V. Mannucci; F. M. Cordero; A. Piperno; G. Romeo; A. Brandi. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 19:(2008), pp. 1204-1209. [10.1016/j.tetasy.2008.04.028]
Diastereoselective synthesis of a collection of new homonucleoside mimetics containing pyrrolo[1,2-b]isoxazoline and pyrrolidine rings.
CORDERO, FRANCA MARIA;BRANDI, ALBERTO
2008
Abstract
The 1,3-dipolar cycloaddition of enantiopure cyclic hydroxylated nitrones and allyl nucleobases has been exploited for the preparation of a novel class of homonucleoside mimetics, where the furanose ring is replaced by a pyrrolo[1,2-b]isoxazolidine system. The nitrones were easily prepared starting from L-malic and L-tartaric acids and gave cycloadducts in a diastereoselective manner, which were deprotected to give good yields of the homo-N,O-nucleoside mimetics. The reduction of the isoxazolidine ring, a 1,3- aminoalcohol equivalent, allows easy access to other new pyrrolidine nucleoside mimetics.File | Dimensione | Formato | |
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TETAsym_nucleoside mimetics.pdf
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