title: An organotrifluoroborate-based convergent total synthesis of the potent cancer cell growth inhibitory depsipeptides kitastatin and respirantin.
abstract: The total syntheses of the highly cytotoxic neo-antimycin macrocyclic depsipeptide natural products kitastatin and respirantin have been accomplished in a convergent manner using MNBA promoted esterifications and an efficient C- and N-terminus bis-deprotection/HATU promoted macrolactamization. The first examples of using a prenyltrifluoroborate reagent in additions to carbonyl groups are disclosed including a diastereoselective multigram scale montmorillonite K10 catalyzed prenylation of N-Boc-l-leucinal to install the structurally unique gem-dimethyl-β-keto-ester fragment.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto ON, Canada , M5S 3H6.
authors.forename: Ramsay E
authors.initials: RE
authors.lastname: Beveridge
authors.forename: Robert A
authors.initials: RA
authors.lastname: Batey
mesh_terms: D000968:Antimycin A / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D001688:Biological Products / Q000737:chemistry* / Q000494:pharmacology*; D001881:Borates / Q000737:chemistry*; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007930:Leucine / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D001688:Biological Products; D001881:Borates; D047630:Depsipeptides; D006845:Hydrocarbons, Fluorinated; C521973:kitastatin 1; C081425:respirantin; D000968:Antimycin A; C035766:leucinal; D007930:Leucine