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  • Title: Domino Pd-catalyzed Heck cyclization and bismuth-catalyzed hydroamination: formal synthesis of elacomine and isoelacomine.
    Author: Kamisaki H, Nanjo T, Tsukano C, Takemoto Y.
    Journal: Chemistry; 2011 Jan 10; 17(2):626-33. PubMed ID: 21207582.
    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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