title: Total synthesis of fellutamide B and deoxy-fellutamides B, C, and D.
abstract: The total syntheses of the marine-derived lipopeptide natural product fellutamide B and deoxy-fellutamides B, C, and D are reported. These compounds were accessed through a novel solid-phase synthetic strategy using Weinreb amide-derived resin. As part of the synthesis, a new enantioselective route to (3R)-hydroxy lauric acid was developed utilizing a Brown allylation reaction followed by an oxidative cleavage-oxidation sequence as the key steps. The activity of these natural products, and natural product analogues was also assessed against Mycobacterium tuberculosis in vitro.
authors.affiliation: School of Chemistry, The University of Sydney, NSW 2006, Australia. agil4696@uni.sydney.edu.au
authors.forename: Andrew M
authors.initials: AM
authors.lastname: Giltrap
authors.forename: Katie M
authors.initials: KM
authors.lastname: Cergol
authors.forename: Angel
authors.initials: A
authors.lastname: Pang
authors.forename: Warwick J
authors.initials: WJ
authors.lastname: Britton
authors.forename: Richard J
authors.initials: RJ
authors.lastname: Payne
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D007850:Lauric Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D055666:Lipopeptides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D013237:Stereoisomerism
chemical_list: D000890:Anti-Infective Agents; D001688:Biological Products; D007850:Lauric Acids; D055666:Lipopeptides; C513652:fellutamide B; C030358:lauric acid