Lewis acid-promoted tandem desulfurization and hydroxylation of γ-phenylthio-substituted lactams: novel synthetic strategy of isoindolobenzazepine alkaloid, chilenine |
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Authors: | Hidemi Yoda Kei-ichi InoueYasuaki Ujihara Nobuyuki MaseKunihiko Takabe |
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Affiliation: | Department of Molecular Science, Faculty of Engineering, Shizuoka University, Johoku 3-5-1, Hamamatsu 432-8561, Japan |
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Abstract: | Treatment of a variety of alicyclic and aromatic γ-phenylthio-substituted lactams with Lewis acids such as cuprous or cupric halides in aqueous solution at rt was found to undergo novel tandem desulfurization and hydroxylation reactions to generate γ-hydroxylated lactams without the ring-opened products in extremely high yields, respectively. This process was further applied to the total synthesis of an isoindolobenzazepine alkaloid, chilenine, by featuring the elaboration of the functionalized phthalimide derivative. |
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