One‐Pot Synthesis of Camalexins and 3, 3′‐Biindoles by the Masuda Borylation–Suzuki Arylation (MBSA) Sequence1. Issue 21 (19th March 2013)

• Record Type: Journal Article
• Authors: Tasch, Boris O. A.; Antovic, Dragutin; Merkul, Eugen; Müller, Thomas J. J.
• Is Part Of: European journal of organic chemistry. Issue 21(2013)
• Page Start: 4564
• Page End: 4569
• Publication Date: 2013-03-19
• Subjects: Synthetic methods -- C–C cou­pling -- Arylation -- Palladium -- Boron -- Alkaloids; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300133
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : The Masuda borylation/Suzuki arylation sequence furnishes in a concise one‐pot manner camalexins and 3, 3′‐biindoles, compounds that show pronounced antifungal, antimicrobial, and cytotoxic activities.