Domino Pd-catalyzed Heck cyclization and bismuth-catalyzed hydroamination: formal synthesis of elacomine and isoelacomine |
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Authors: | Kamisaki Haruhi Nanjo Takeshi Tsukano Chihiro Takemoto Yoshiji |
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Affiliation: | Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan. |
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Abstract: | The formal synthesis of hemiterpene spirooxindole alkaloids elacomine (1) and isoelacomine (2) is described. Heck reaction of protected iodoanilines with 5,6-dihydro-2H-pyran-2-one or six-membered unsaturated lactams was investigated. The coupling product was readily converted to a carbamoyl chloride with an incorporated diene unit. The spiro(pyrrolidine-3,3'-oxindole) skeleton, which corresponds to the carbon skeleton of 1 and 2, was efficiently constructed from this intermediate by using a domino palladium-catalyzed Heck reaction and bismuth-catalyzed hydroamination. An isolated byproduct of the reaction could also be converted to the spirooxindole skeleton. |
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Keywords: | bismuth domino reactions formal synthesis palladium spiro compounds |
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