title: InCl3-mediated addition of indole to isatogens: an expeditious synthesis of 13-deoxy-isatisine A.
abstract: A strategy directed towards the total synthesis of isatisine A that involves several late-stage metal-catalyzed transformations that address the key carbon-carbon and carbon-heteroatom bond formations has been developed. As a part of this strategy, methods for the addition of indoles to isatogens that lead selectively to either 2,2-disubstituted N-hydroxyindolin-3-one or 2,2-disubstituted indolin-3-one compounds have been developed by employing InCl(3)  as a catalyst or as the reagent. The present methods provide the first examples of the additions of indoles to the isatogen nucleus. To demonstrate its viability, the synthesis of 13-deoxy-isatisine A has been completed in ten steps from a known and easily available lactone.
authors: Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411 008, India.
authors: Chepuri V Suneel
authors: CV
authors: Kumar
authors: Vedavati G
authors: VG
authors: Puranik
authors: Chepuri V
authors: CV
authors: Ramana
mesh_terms: D002384:Catalysis; D007204:Indium / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D007510:Isatin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D026121:Indole Alkaloids; D007211:Indoles; C456900:indolin-2-one; D007204:Indium; C020758:indium trichloride; D007510:Isatin