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Gold‐Catalyzed Cyclopenta‐ and Cycloheptannulation Cascades: A Stereocontrolled Approach to the Scaffold of Frondosins A and B
Author(s) -
Garayalde David,
Krüger Karolin,
Nevado Cristina
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201006105
Subject(s) - propargyl , cascade , enantioselective synthesis , catalysis , formal synthesis , chemistry , stereochemistry , combinatorial chemistry , organic chemistry , chromatography
Golden cascades : Two diastereoselective gold‐catalyzed cascade processes in which propargyl acetates react with alkenes or 1,4‐dienes afford highly substituted five‐ and seven‐membered rings, respectively (see scheme). The concerted nature of the gold‐catalyzed Cope rearrangement has been used in the formal enantioselective synthesis of marine norsesquiterpenoids Frondosins A and B.