title: Total synthesis of RNA-polymerase inhibitor ripostatin B and 15-deoxyripostatin A.
abstract: Keep me skipped: a highly convergent total synthesis of ripostatin B, an inhibitor of the bacterial RNA polymerase, is described. The key steps to construct and avoid isomerization of the skipped triene are a double Stille cross-coupling reaction and a ring-closing metathesis. Furthermore, 15-deoxyripostatin A, a stable and conformationally locked analogue of ripostatin A, was prepared and tested in vivo.
authors.affiliation: Department of Medicinal Chemistry, Helmholtz Centre for Infection Research, Braunschweig, Germany.
authors.forename: Wufeng
authors.initials: W
authors.lastname: Tang
authors.forename: Evgeny V
authors.initials: EV
authors.lastname: Prusov
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D012321:DNA-Directed RNA Polymerases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009231:Myxococcales / Q000201:enzymology; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism
chemical_list: C578403:15-deoxyripostatin A; D000900:Anti-Bacterial Agents; D004791:Enzyme Inhibitors; D007783:Lactones; C096601:ripostatin B; D012321:DNA-Directed RNA Polymerases