title: Modular Total Synthesis of Protein Kinase C Activator (-)-Indolactam V.
abstract: A concise, eight-step total synthesis of (-)-indolactam V, a nanomolar agonist of protein kinase C, is reported. The synthesis relies upon an efficient copper-catalyzed amino acid arylation to establish the indole C4-nitrogen bond. This cross-coupling method is applicable to a range of hydrophobic amino acids, providing a platform for further diversification of indolactam alkaloid scaffolds and studies on their potent biological activity.
authors.affiliation: Department of Chemistry and Biochemistry, San Francisco State University , San Francisco, California 94132, United States.
authors.forename: Jeremy
authors.initials: J
authors.lastname: Haynes-Smith
authors.affiliation: Department of Chemistry and Biochemistry, San Francisco State University , San Francisco, California 94132, United States.
authors.forename: Italia
authors.initials: I
authors.lastname: Diaz
authors.affiliation: Department of Chemistry and Biochemistry, San Francisco State University , San Francisco, California 94132, United States.
authors.forename: Kelvin L
authors.initials: KL
authors.lastname: Billingsley
mesh_terms: D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D011493:Protein Kinase C / Q000378:metabolism; D047428:Protein Kinase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D007769:Lactams; D047428:Protein Kinase Inhibitors; C043969:indolactam V; D011493:Protein Kinase C