A new series of conformationally locked N,O-nucleoside analogues was synthesized by exploiting allenic nucleobases as dipolarophiles in 1,3-dipolar nitrone cycloadditions. The regio- and sitoselectivity of the reaction were rationalized according to the frontier orbital treatment of the nitrone cycloaddition by AM1 calculations.
Synthesis of methyleneisoxazolidine nucleoside analogues by microwave-assisted nitrone cycloaddition
IANNAZZO, Daniela;PIPERNO, Anna;ROMEO, Giovanni;ROMEO, Roberto;
2007-01-01
Abstract
A new series of conformationally locked N,O-nucleoside analogues was synthesized by exploiting allenic nucleobases as dipolarophiles in 1,3-dipolar nitrone cycloadditions. The regio- and sitoselectivity of the reaction were rationalized according to the frontier orbital treatment of the nitrone cycloaddition by AM1 calculations.File in questo prodotto:
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