title: Cu-mediated enamide formation in the total synthesis of complex peptide natural products.
abstract: Cu-mediated C(sp(2))-N bond formation has received intense interest recently, and has been applied to the total synthesis of a wide variety of structurally complex natural products. This review covers the synthetic assembly of peptide natural products in which Cu-mediated enamide formation is the key transformation. The total syntheses of cyclopeptide alkaloids, pacidamycin D, and yaku'amide A exemplify the versatility of the Cu-catalyzed cross-coupling reaction in comparison to other synthetic methods.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. inoue@mol.f.u-tokyo.ac.jp.
authors.forename: Takefumi
authors.initials: T
authors.lastname: Kuranaga
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Sesoko
authors.forename: Masayuki
authors.initials: M
authors.lastname: Inoue
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001688:Biological Products; D009842:Oligopeptides; D010455:Peptides; D010456:Peptides, Cyclic; D011741:Pyrimidine Nucleosides; C569211:pacidamycin D; C556702:yaku'amide A; D003300:Copper