A facile synthesis of (±)-sesbanine via γ-addition of ketene silyl acetal with quaternized methyl nicotinate |
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Authors: | Makoto Wada Yoshihiro Nishihara Kin-ya Akiba |
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Institution: | Department of Chemistry, Faculty of Science, Hiroshima University Higashisenda-machi, Hiroshima 730, Japan |
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Abstract: | Total synthesis of (±)-sesbanine () was carried out using γ-addition of ketene silyl acetal of methyl 3-cyclopentenecarboxylate to quaternized methyl nicotinate. The resulting 1,4-dihydropyridine () was oxidized with DDQ to give 4-substituted nicotinate () and was converted to alcohol () by stereoselective oxymercuration followed by treatment with ammonia to give . |
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