Traceless solid-phase synthesis of hydroxylated cyclopentenones |
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Authors: | Christos I Stathakis |
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Institution: | Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki GR 541 24, Greece |
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Abstract: | Intramolecular nitrone-alkene cycloadditions on solid phase can be performed using polymer-bound hydroxylamine. Condensation of this reagent with sugar derived 4-pentenals followed by N-O cleavage, quaternization of the amine thus produced, and finally oxidative elimination of the amino group detaches the chiral hydroxylated cyclopentenones from the polymer. The natural antibiotic pentenomycin I was prepared in this way. |
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