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Selectivity in the Aerobic Dearomatization of Phenols: Total Synthesis of Dehydronornuciferine by Chemo‐ and Regioselective Oxidation
Author(s) -
Esguerra Kenneth Virgel N.,
Lumb JeanPhilip
Publication year - 2018
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.201710271
Subject(s) - aporphine , selectivity , regioselectivity , chemistry , phenols , catalysis , context (archaeology) , combinatorial chemistry , substrate (aquarium) , phenanthrenes , organic chemistry , phenanthrene , paleontology , oceanography , biology , alkaloid , geology
We describe a selective aerobic oxidation of meta‐biaryl phenols that enables rapid access to functionalized phenanthrenes. Aerobic oxidations attract interest due to their efficiency, but remain underutilized in complex molecule settings due to challenges of selectivity. We discuss these issues in the context of Cu catalysis, and highlight the advantages of confining oxygen activation and substrate oxidation to the catalyst's inner‐coordination sphere. This gives rise to predictable selectivity that we use for a concise synthesis of the aporphine dehydronornuciferine.