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Synthesis of fused bicyclic glutarimides
Authors:Meng-Yang Chang  Chung-Yi ChenShui-Tein Chen  Nein-Chen Chang
Affiliation:a Department of Applied Chemistry, National University of Kaohsiung, Kaohsiung 811, Taiwan, ROC
b Department of Chemistry, National Sun Yat-Sen University, Kaohsiung 804, Taiwan, ROC
c Institute of Biological Chemistry, Academia Sinica, Nankang, Taipei 115, Taiwan, ROC
Abstract:We describe an efficient route towards the synthesis of fused bicyclic glutarimides using facile [3+3] reaction of α-sulfonylacetamides with different α,β-unsaturated esters as the key step. Intramolecular cyclization of 4-substituted 3-sulfonylglutarimide to form 5,6-, 6,6- or 6,7-fused bicyclic glutarimides was accomplished via alkylation, oxidative cyclization or ring-closing metathesis in modest yield.
Keywords:bicyclic glutarimides   stepwise [3+3] annulation   intramolecular alkylation   oxidative cyclization or ring-closing metathesis
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