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

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 tre...

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Bibliographic Details
Published in:Tetrahedron 2008-10, Vol.64 (42), p.9989-9991
Main Authors: Falentin, Céline, Beaupère, Daniel, Demailly, Gilles, Stasik, Imane
Format: Article
Language:English
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Summary: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 NaN 3 to give 2-azido-2-deoxy- d-lyxono and xylono-1,4-lactones. Saponification of the obtained 2-azido derivatives gave the corresponding 2-azido-2-deoxyaldonic acids salt which, after neutralization followed by reduction, led to the expected compounds: (−)-polyoxamic acid ( 3) and 3,4-diepipolyoxamic acid ( 2) in 38% and 29% overall yields. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.07.095