title: Synthesis of S-(-)-5,6-Dihydrocanthin-4-ones via a Triple Cooperative Catalysis-Mediated Domino Reaction.
abstract: An enantioselective synthesis of S-(-)-5,6-dihydrocanthin-4-ones via a triple cooperative catalysis-mediated domino reaction having a broad substrate scope is reported. The reaction between substituted 1-formyl-9H-β-carbolines and terminal alkynes in the presence of catalytic amounts of Jorgensen-Hayashi catalyst, copper iodide, and Hunig base proceeded via a multicascade route, affording the title compounds in good yields and excellent ees with interesting mechanistic features. These compounds were assessed for in vitro antiplasmodial activity against P. falciparum strains. Additionally, 5,6-dihydrocanthin-4-ones are demonstrated to be a versatile precursor to different fused β-carboline derivatives via simple synthetic transformations.
authors.forename: Shashikant U
authors.initials: SU
authors.lastname: Dighe
authors.forename: Rohit
authors.initials: R
authors.lastname: Mahar
authors.affiliation: Academy of Scientific and Innovative Research , New Delhi 110025, India.
authors.forename: Sanjeev K
authors.initials: SK
authors.lastname: Shukla
authors.forename: Ruchir
authors.initials: R
authors.lastname: Kant
authors.affiliation: Academy of Scientific and Innovative Research , New Delhi 110025, India.
authors.forename: Kumkum
authors.initials: K
authors.lastname: Srivastava
authors.affiliation: Academy of Scientific and Innovative Research , New Delhi 110025, India.
authors.forename: Sanjay
authors.initials: S
authors.lastname: Batra
mesh_terms: D000962:Antimalarials / Q000138:chemical synthesis* / Q000494:pharmacology*; D002243:Carbolines / Q000138:chemical synthesis* / Q000494:pharmacology*; D002384:Catalysis; D003300:Copper; D007202:Indicators and Reagents; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology*; D007454:Iodides; D010963:Plasmodium falciparum / Q000187:drug effects; D013237:Stereoisomerism
chemical_list: D000962:Antimalarials; D002243:Carbolines; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007454:Iodides; C000614893:canthin-4-one; D003300:Copper