title: Total synthesis of the bacterial RNA polymerase inhibitor ripostatin B.
abstract: A modular and highly stereoselective synthesis of the title compound was developed. Key steps in the assembly of the carbon framework of ripostatin B were a stereoselective Paterson aldol reaction and a high-yielding ring-closing metathesis mediated by Grubbs first generation catalyst. The C15 hydroxy group was established through Tishchenko-Evans reduction in excellent yield and selectivity.
authors.affiliation: Swiss Federal Institute of Technology Zürich, Department of Chemistry and Applied Biosciences, Institute of Pharmaceutical Sciences, Switzerland.
authors.forename: Florian
authors.initials: F
authors.lastname: Glaus
authors.forename: Karl-Heinz
authors.initials: KH
authors.lastname: Altmann
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry; D012321:DNA-Directed RNA Polymerases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D009231:Myxococcales / Q000201:enzymology; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D004791:Enzyme Inhibitors; D004852:Epoxy Compounds; D007783:Lactones; C096601:ripostatin B; D012321:DNA-Directed RNA Polymerases