Synthesis of novel isoxazolidine analogues of homonucleosides |
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Authors: | Joanna Gotkowska Jan Balzarini Dorota G. Piotrowska |
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Affiliation: | 1. Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of ?ód?, 90-151 ?ód?, Muszyńskiego 1, Poland;2. Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium |
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Abstract: | A general method for the synthesis of nucleobase-derived nitrones 4a–e by treatment of N-(2-oxoethyl)nucleobases with N-methylhydroxylamine is reported. The nitrones 4a–e were applied in the synthesis of isoxazolidine homonucleosides. Moderate diastereoselectivities (de 28–82%) were observed for cycloadditions between nitrones 4a–e and allyl alcohol with cis-isoxazolidines predominating. The stereochemistry of the substituted isoxazolidines was established based on an analysis of 2D NOE experiments for uracil-containing cycloadducts 6a and 7a. Cycloadditions of uracil-based nitrone 4a with vinyl-, allyl-, vinyloxymethyl- and allyloxymethylphosphonates gave the respective phosphonylated cis-isoxazolidines as the major adducts. |
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