title: Total synthesis of aurachins C, D, and L, and a structurally simplified analog of aurachin C.
abstract: The quinoline antibiotics aurachins C, D, and L, and a structurally simplified analog of aurachin C were synthesized from 1-(2-nitrophenyl)butane-1,3-dione via reductive cyclizations of δ-nitro ketone intermediates, with zinc or iron as key steps. The results of antimicrobial tests indicate that the N-hydroxyquinolone nucleus mimics the electron carrier in the respiratory chain more strongly than the quinoline N-oxide nucleus.
authors.affiliation: a Biomaterial Engineering Research Group , Bioproduction Research Institute, National Institute of Advanced Industrial Science and Technology (AIST) , Toyohira-ku, Sapporo , Japan.
authors.forename: Masaru
authors.initials: M
authors.lastname: Enomoto
authors.forename: Wataru
authors.initials: W
authors.lastname: Kitagawa
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Yasutake
authors.forename: Hiroki
authors.initials: H
authors.lastname: Shimizu
mesh_terms: D060326:Chemistry Techniques, Synthetic; D003500:Cyclization; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D011804:Quinolines; D015363:Quinolones; C000596975:aurachin L; C052097:aurachin D; C052096:aurachin C
keywords: aurachins; quinoline antibiotics; reductive cyclization