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Efficient Total Syntheses of (−)‐Colombiasin A and (−)‐Elisapterosin B: Application of the Cr‐Catalyzed Asymmetric Quinone Diels–Alder Reaction
Author(s) -
Boezio Alessandro A.,
Jarvo Elizabeth R.,
Lawrence Brian M.,
Jacobsen Eric N.
Publication year - 2005
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.200502178
Subject(s) - quinone , diels–alder reaction , catalysis , chemistry , total synthesis , organic chemistry , stereochemistry , combinatorial chemistry
A made‐to‐order asymmetric catalytic reaction was applied in the key quinone Diels–Alder step of the total syntheses of the title compounds (see scheme for the synthesis of colombiasin A). The reaction was highly regio‐ and diastereoselective.