期刊
TETRAHEDRON LETTERS
卷 53, 期 52, 页码 7097-7100出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.10.074
关键词
1,3-Dipolar cycloadditions; Nitrones; Isoxazolidines; Homonucleoside analogues
资金
- Medical University of Lodz [503/3-014-1/503-01, 502-03-/3-014-01/502-34-031]
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. (C) 2012 Elsevier Ltd. All rights reserved.
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