title: Enantioselective syntheses of the alkaloids cis-195A (pumiliotoxin C) and trans-195A based on multiple applications of asymmetric catalysis.
abstract: Short enantio- and diastereoselective syntheses of the decahydroquinoline alkaloids cis- (pumiliotoxin C) and trans-195A are presented. Key steps are an enantioselective iridium-catalyzed allylic amination, a Suzuki-Miyaura coupling, a catalyst-controlled copper-catalyzed 1,4-addition, and a reductive amination.
authors.affiliation: Organisch-Chemisches Institut der Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany.
authors.forename: Martin
authors.initials: M
authors.lastname: Gärtner
authors.forename: Jianping
authors.initials: J
authors.lastname: Qu
authors.forename: Günter
authors.initials: G
authors.lastname: Helmchen
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000586:Amination; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D003300:Copper / Q000737:chemistry; D007495:Iridium / Q000737:chemistry; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D011804:Quinolines; C011093:pumiliotoxin C; D007495:Iridium; C037920:decahydroquinoline-5-carboxylic acid; D003300:Copper