Total Synthesis of Tetarimycin A, (±)-Naphthacemycin A9, and (±)-Fasamycin A: Structure–Activity Relationship Studies against Drug-Resistant Bacteria

Making use of a reductive olefin coupling reaction and Michael–Dieckmann condensation as two key operations, we have completed a concise total synthesis of tetarimycin A, (±)-naphthacemycin A9, and (±)-fasamycin A in a highly convergent and practical protocol. Synthetic procedures thus developed hav...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-06, Vol.83 (12), p.6508-6523
Main Authors: Huang, Jing-Kai, Yang Lauderdale, Tsai-Ling, Lin, Chun-Cheng, Shia, Kak-Shan
Format: Article
Language:English
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Summary:Making use of a reductive olefin coupling reaction and Michael–Dieckmann condensation as two key operations, we have completed a concise total synthesis of tetarimycin A, (±)-naphthacemycin A9, and (±)-fasamycin A in a highly convergent and practical protocol. Synthetic procedures thus developed have also been applied to provide related analogues for structure–activity relationship studies, thereby coming to the conclusion that the free hydroxyl group at C-10 is essential for exerting inhibitory activities against a panel of Gram-positive bacteria, including drug-resistant strains VRE and MRSA.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b00802