title: Protic-solvent-mediated cycloisomerization of quinoline and isoquinoline propargylic alcohols: syntheses of (±)-3-demethoxyerythratidinone and (±)-cocculidine.
abstract: Putting the "benz" in indolizinones: A cycloisomerization approach to benz[g]indolizinones and benz[e]indolizinones provides the first general route to these unique azacycles (see example). The utility of the benzindolizinone products was demonstrated by the application of this method to the total synthesis of the Erythrina alkaloids 3-demethoxyerythratidinone and cocculidine.
authors.affiliation: Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA).
authors.forename: Stephen T
authors.initials: ST
authors.lastname: Heller
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Kiho
authors.forename: Alison R H
authors.initials: AR
authors.lastname: Narayan
authors.forename: Richmond
authors.initials: R
authors.lastname: Sarpong
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000737:chemistry*; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry*
chemical_list: C514302:3-demethoxyerythratidinone; D000470:Alkaloids; D000480:Alkynes; D026121:Indole Alkaloids; D007546:Isoquinolines; D020005:Propanols; D011804:Quinolines; C015083:cocculitine; C037219:quinoline; C028255:propargyl alcohol; C039109:isoquinoline
keywords: Erythrina alkaloids; Schrock catalysts; cycloisomerization; heterocycles; molybdenum