title: Total synthesis of (±)-hirsutine: application of phosphine-catalyzed imine-allene [4 + 2] annulation.
abstract: The total synthesis of the indole alkaloid hirsutine has been achieved, with a key step being the application of our phosphine-catalyzed [4 + 2] annulation of an imine with ethyl α-methylallenoate. From commercially available indole-2-carboxaldehyde, the target was synthesized in 14 steps and 6.7% overall yield.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
authors.forename: Reymundo A
authors.initials: RA
authors.lastname: Villa
authors.forename: Qihai
authors.initials: Q
authors.lastname: Xu
authors.forename: Ohyun
authors.initials: O
authors.lastname: Kwon
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism; D032070:Uncaria / Q000737:chemistry
chemical_list: D000466:Alkadienes; D000470:Alkaloids; D007097:Imines; D010720:Phosphines; C044646:phosphine; C038369:hirsutine