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Synthesis of S-(−)-5,6-Dihydrocanthin-4-ones via a Triple Cooperative Catalysis-Mediated Domino Reaction

Author:
Dighe, Shashikant U., Mahar, Rohit, Shukla, Sanjeev K., Kant, Ruchir, Srivastava, Kumkum, Batra, Sanjay
Source:
Journal of organic chemistry 2016 v.81 no.11 pp. 4751-4761
ISSN:
1520-6904
Subject:
Plasmodium falciparum, alkynes, antiparasitic properties, catalysts, chemical reactions, chemical structure, copper, enantioselective synthesis, iodides, organic chemistry
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.
Agid:
5505537