Application of a Palladium‐Catalyzed C−H Functionalization/Indolization Method to Syntheses of  cis ‐Trikentrin A and Herbindole B | Zendy

Leal Raul A. | Zendy; Bischof Caroline | Zendy; Lee Youjin V. | Zendy; Sawano Shota | Zendy; McAtee Christopher C. | Zendy; Latimer Luke N. | Zendy; Russ Zachary N. | Zendy; Dueber John E. | Zendy; Yu JinQuan | Zendy; Sarpong Richmond | Zendy

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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.

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