Tetrahedron

New approach to (−)-polyoxamic acid and 3, 4-diepipolyoxamic acid from d-lyxono-1, 4-lactone

C Falentin, D Beaupere, G Demailly, I Stasik

文献索引：Falentin, Celine; Beaupere, Daniel; Demailly, Gilles; Stasik, Imane Tetrahedron, 2008 , vol. 64, # 42 p. 9989 - 9991

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被引用次数: 9

摘要

The non-natural enantiomer of polyoxamic acid (1) and 3, 4-diepipolyoxamic acid (2) was synthesized in four steps from d-lyxono-1, 4-lactone (4). Regioselective bromination of unprotected d-lyxono-1, 4-lactone with HBr/AcOH led to 2-bromo-2-deoxy-d-xylono-1, 4- lactone (5). This intermediate was treated with NaN3 to give 2-azido-2-deoxy-d-lyxono and xylono-1, 4-lactones. Saponification of the obtained 2-azido derivatives gave the ...