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Application of a Palladium‐Catalyzed C−H Functionalization/Indolization Method to Syntheses of cis ‐Trikentrin A and Herbindole B
Author(s) -
Leal Raul A.,
Bischof Caroline,
Lee Youjin V.,
Sawano Shota,
McAtee Christopher C.,
Latimer Luke N.,
Russ Zachary N.,
Dueber John E.,
Yu JinQuan,
Sarpong Richmond
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201605475
Subject(s) - amination , desymmetrization , chemistry , hydroquinone , indole test , steric effects , catalysis , palladium , cycloaddition , surface modification , natural product , regioselectivity , combinatorial chemistry , stereochemistry , organic chemistry , enantioselective synthesis
We describe herein formal syntheses of the indole alkaloids cis ‐trikentrin A and herbindole B from a common meso ‐hydroquinone intermediate prepared by a ruthenium‐catalyzed [2+2+1+1] cycloaddition that has not been used previously in natural product synthesis. Key steps include a sterically demanding Buchwald–Hartwig amination as well as a unique C(sp 3 )−H amination/indole formation. Studies toward a selective desymmetrization of the meso ‐hydroquinone are also reported.