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A Synthesis of Echinopine B
Author(s) -
Michels Theo D.,
Dowling Matthew S.,
Vanderwal Christopher D.
Publication year - 2012
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.201203147
Subject(s) - cycloisomerization , annulation , scheme (mathematics) , enyne , chemistry , product (mathematics) , stereochemistry , computer science , bicyclic molecule , combinatorial chemistry , organic chemistry , catalysis , mathematics , mathematical analysis , geometry
In a short synthesis of echinopine B, a guaiane‐like intermediate was generated through a methylenecyclopentane annulation onto a substituted cycloheptenone. The resulting bicyclic compound was converted into the natural product by a PtCl 2 ‐catalyzed enyne cycloisomerization (see scheme). Several late‐stage polycyclic rearrangement products were isolated and characterized.