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A General Cp*Co III ‐Catalyzed Intramolecular C−H Activation Approach for the Efficient Total Syntheses of Aromathecin, Protoberberine, and Tylophora Alkaloids
Author(s) -
Lerchen Andreas,
Knecht Tobias,
Koy Maximilian,
Daniliuc Constantin G.,
Glorius Frank
Publication year - 2017
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.201702648
Subject(s) - intramolecular force , annulation , chemistry , catalysis , alkaloid , stereochemistry , scope (computer science) , total synthesis , combinatorial chemistry , alkyne , functional group , organic chemistry , computer science , polymer , programming language
Herein, we report a Cp*Co III ‐catalyzed C−H activation approach as the key step to create highly valuable isoquinolones and pyridones as building blocks that can readily be applied in the total syntheses of a variety of aromathecin, protoberberine, and tylophora alkaloids. This particular C−H activation/annulation reaction was achieved with several terminal as well as internal alkyne coupling partners delivering a broad scope with excellent functional group tolerance. The synthetic applicability of this protocol reported herein was demonstrated in the total syntheses of two Topo‐I‐Inhibitors and two 8‐oxyprotoberberine cores that can be further elaborated into the tetrahydroprotoberberine and the protoberberine alkaloid core. Moreover these building blocks were also transformed to six different tylophora alkaloids in expedient fashion.