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Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16Z,20E)-Eushearilide and (16E,20E)-Eushearilide

1
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
2
Department of Infectious Diseases, Medical Mycology Research Center, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba-shi, Chiba 260-8673, Japan
*
Authors to whom correspondence should be addressed.
Academic Editor: Marc C. Kimber
Molecules 2019, 24(19), 3437; https://doi.org/10.3390/molecules24193437
Received: 7 August 2019 / Revised: 7 September 2019 / Accepted: 11 September 2019 / Published: 22 September 2019
(This article belongs to the Special Issue Total Synthesis of Biologically Active Product)
A novel stereoisomer of eushearilide, 23-demethyleushearilide, was synthesized, and the structure–activity relationships of this compound along with known eushearilide stereoisomers were investigated in order to design novel lead compounds for the treatment of fungal infections. It was discovered that all of these congeners, together with the natural product, exhibited a wide range of antimicrobial activity against not only fungi but also against bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE). View Full-Text
Keywords: eushearilide; demethyl congener; total synthesis; lactonization; MNBA; antimicrobial activity eushearilide; demethyl congener; total synthesis; lactonization; MNBA; antimicrobial activity
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Tonoi, T.; Inohana, T.; Sato, T.; Noda, Y.; Ikeda, M.; Akutsu, M.; Murata, T.; Maekawa, Y.; Tanaka, A.; Seki, R.; Ohkusu, M.; Kamei, K.; Ishiwada, N.; Shiina, I. Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16Z,20E)-Eushearilide and (16E,20E)-Eushearilide. Molecules 2019, 24, 3437.

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