title: A general catalytic reaction sequence to access alkaloid-inspired indole polycycles.
abstract: A catalytic two-step reaction sequence was developed to access a range of complex heterocyclic frameworks based on biorelevant indole/oxindole scaffolds. The reaction sequence includes catalytic Pictet-Spengler cyclization followed by Au(I) catalyzed intramolecular hydroamination of acetylenes. A related cascade polycyclization of a designed β-carboline embodying a 1,5-enyne group yields the analogues of the alkaloid harmicine.
authors.affiliation: Max Planck Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn Str. 11, 44227-Dortmund, Germany. kamal.kumar@mpi-dortmund.mpg.de Herbert.waldmann@mpi-dortmund.mpg.de.
authors.forename: Adithi
authors.initials: A
authors.lastname: Danda
authors.forename: Kamal
authors.initials: K
authors.lastname: Kumar
authors.forename: Herbert
authors.initials: H
authors.lastname: Waldmann
mesh_terms: D000114:Acetylene / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D000586:Amination; D002243:Carbolines / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D011807:Quinolizines / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000470:Alkaloids; D002243:Carbolines; D026121:Indole Alkaloids; D007211:Indoles; D011807:Quinolizines; C544842:harmicine; D006046:Gold; C030374:indole; D000114:Acetylene