title: Total synthesis of (-)-isatisine A.
abstract: A modular total synthesis of (-)-isatisine A is described in which four consecutive metal-mediated transformations have been employed at the final stage. These include [Pd]-catalyzed Sonogashira coupling, [Pd]-catalyzed nitroalkyne cycloisomerization leading to isatogens, and addition of indoles to isatogens using InCl(3)- and [Rh]-catalyzed oxidative N-heterocyclization of amino alcohol to form the key amide bond. In addition to these, the removal of the protecting groups has also been carried out in a selective fashion employing either catalytic or stoichiometric metal/metal-based reagents.
authors.affiliation: Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhaba Road, Pune-411008, India.
authors.forename: Pitambar
authors.initials: P
authors.lastname: Patel
authors.forename: C V
authors.initials: CV
authors.lastname: Ramana
mesh_terms: D000577:Amides / Q000737:chemistry*; D000605:Amino Alcohols / Q000737:chemistry*; D002384:Catalysis; D007202:Indicators and Reagents / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*
chemical_list: D000577:Amides; D000605:Amino Alcohols; D007202:Indicators and Reagents; D026121:Indole Alkaloids; C524145:isatisine A; D010165:Palladium; D007510:Isatin