Total synthesis of aurachins C, D, and L, and a structurally simplified analog of aurachin C.
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.
['Enomoto|Masaru|M|', 'Kitagawa|Wataru|W|', 'Yasutake|Yoshiaki|Y|', 'Shimizu|Hiroki|H|']
D060326:Chemistry Techniques, Synthetic D003500:Cyclization D011804:Quinolines D015363:Quinolones
aurachins quinoline antibiotics reductive cyclization