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A facile synthesis of (±)-sesbanine via γ-addition of ketene silyl acetal with quaternized methyl nicotinate
Authors:Makoto Wada  Yoshihiro Nishihara  Kin-ya Akiba
Institution:Department of Chemistry, Faculty of Science, Hiroshima University Higashisenda-machi, Hiroshima 730, Japan
Abstract:Total synthesis of (±)-sesbanine (1) was carried out using γ-addition of ketene silyl acetal of methyl 3-cyclopentenecarboxylate to quaternized methyl nicotinate. The resulting 1,4-dihydropyridine (7) was oxidized with DDQ to give 4-substituted nicotinate (2) and 2 was converted to alcohol (8) by stereoselective oxymercuration followed by treatment with ammonia to give 1.
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