TY - JOUR
T1 - Total synthesis of aurachins C, D, and L, and a structurally simplified analog of aurachin C
AU - Enomoto, Masaru
AU - Kitagawa, Wataru
AU - Yasutake, Yoshiaki
AU - Shimizu, Hiroki
N1 - Funding Information:
This work was supported, in part, by a grant-in-aid for Young Scientists (B) from the Ministry of Education, Culture, Sports, Science and Technology of Japan [grant number 23780112].
Publisher Copyright:
© 2014 Japan Society for Bioscience, Biotechnology, and Agrochemistry.
PY - 2014
Y1 - 2014
N2 - 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.
AB - 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.
KW - Aurachins
KW - Quinoline antibiotics
KW - Reductive cyclization
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U2 - 10.1080/09168451.2014.918494
DO - 10.1080/09168451.2014.918494
M3 - Article
C2 - 25130733
AN - SCOPUS:84928053873
SN - 0916-8451
VL - 78
SP - 1324
EP - 1327
JO - Bioscience, Biotechnology and Biochemistry
JF - Bioscience, Biotechnology and Biochemistry
IS - 8
ER -