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Domino Pd‐Catalyzed Heck Cyclization and Bismuth‐Catalyzed Hydroamination: Formal Synthesis of Elacomine and Isoelacomine
Author(s) -
Kamisaki Haruhi,
Nanjo Takeshi,
Tsukano Chihiro,
Takemoto Yoshiji
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201002287
Subject(s) - hydroamination , oxindole , chemistry , pyrrolidine , catalysis , domino , heck reaction , organic chemistry , palladium , combinatorial chemistry , medicinal chemistry
The formal synthesis of hemiterpene spirooxindole alkaloids elacomine ( 1 ) and isoelacomine ( 2 ) is described. Heck reaction of protected iodoanilines with 5,6‐dihydro‐2 H ‐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.