title: Ir-catalyzed reverse prenylation of 3-substituted indoles: total synthesis of (+)-aszonalenin and (-)-brevicompanine B.
abstract: The selective reverse prenylation of 3-substituted-1H-indoles at C3 is described. The iridium-catalyzed reaction proceeds with high branched to linear selectivity (>20:1) for a variety of indoles. In addition, a diastereoselective reverse prenylation of tryptophan methyl ester is disclosed, and its synthetic utility is demonstrated in the synthesis of (+)-aszonalenin and (-)-brevicompanine B.
authors.affiliation: Eidgenössische Technische Hochschule Zürich , 8093 Zürich, Switzerland.
authors.forename: Jonathan
authors.initials: J
authors.lastname: Ruchti
authors.forename: Erick M
authors.initials: EM
authors.lastname: Carreira
mesh_terms: D002384:Catalysis; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D007495:Iridium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D026121:Indole Alkaloids; D007211:Indoles; D009942:Organometallic Compounds; C000602357:brevicompanine B; C000602356:aszonalenin; D007495:Iridium