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One‐Pot Synthesis of Camalexins and 3,3′‐Biindoles by the Masuda Borylation–Suzuki Arylation (MBSA) Sequence
Author(s) -
Tasch Boris O. A.,
Antovic Dragutin,
Merkul Eugen,
Müller Thomas J. J.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300133
Subject(s) - borylation , chemistry , antifungal , sequence (biology) , combinatorial chemistry , suzuki reaction , catalysis , stereochemistry , organic chemistry , palladium , biochemistry , microbiology and biotechnology , aryl , alkyl , biology
The Masuda borylation/Suzuki arylation (MBSA) sequence starting from N ‐protected 3‐iodoindoles has successfully been extended to the coupling of five‐membered heterocycles and indoles in the arylation step, which could not be achieved with previously developed MBSA methods. By this approach the one‐pot nature of the method as well as the use of a simple catalyst system has been retained. The applicability of the method has been demonstrated by the facile synthesis of camalexins and 3,3′‐biindoles, compounds of special interest due to their pronounced antifungal, antimicrobial and cytotoxic activities.