title: Total syntheses of linear polythiazole/oxazole plantazolicin A and its biosynthetic precursor plantazolicin B.
abstract: Plantazolicin A, a linear decacyclic natural product, exhibits desirable selective activity against the causative agent of anthrax toxicity. The total synthesis of plantazolicin A and its biosynthetic precursor plantazolicin B was successfully achieved by an efficient, unified, and highly convergent route featuring dicyclizations to form 2,4-concatenated oxazoles and the mild synthesis of thiazoles from natural amino acids. This report represents the first synthesis of plantazolicin B and includes the first complete characterization data for both natural products.
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW (UK).
authors.forename: Zoe E
authors.initials: ZE
authors.lastname: Wilson
authors.forename: Sabine
authors.initials: S
authors.lastname: Fenner
authors.forename: Steven V
authors.initials: SV
authors.lastname: Ley
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001408:Bacillus anthracis / Q000187:drug effects; D003500:Cyclization; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010080:Oxazoles / Q000737:chemistry; D010084:Oxidation-Reduction; D013457:Sulfur Compounds / Q000737:chemistry; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C419465:(bis(2-methoxyethyl)amino)sulfur trifluoride; D000596:Amino Acids; D000900:Anti-Bacterial Agents; D006845:Hydrocarbons, Fluorinated; D009842:Oligopeptides; D010080:Oxazoles; D013457:Sulfur Compounds; D013844:Thiazoles; C560834:plantazolicin A; C560835:plantazolicin B
keywords: cyclization; heterocycles; natural products; peptides; total synthesis