Total Synthesis of (−)-Caprazamycin A†
Hugh Nakamura
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan)
Search for more papers by this authorDr. Chihiro Tsukano
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan)
Search for more papers by this authorMotohiro Yasui
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan)
Search for more papers by this authorShinsuke Yokouchi
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan)
Search for more papers by this authorDr. Masayuki Igarashi
Institute of Microbial Chemistry (BIKAKEN), Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Dr. Yoshiji Takemoto
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan)
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan)Search for more papers by this authorHugh Nakamura
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan)
Search for more papers by this authorDr. Chihiro Tsukano
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan)
Search for more papers by this authorMotohiro Yasui
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan)
Search for more papers by this authorShinsuke Yokouchi
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan)
Search for more papers by this authorDr. Masayuki Igarashi
Institute of Microbial Chemistry (BIKAKEN), Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Dr. Yoshiji Takemoto
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan)
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan)Search for more papers by this authorThis work was supported by a Grant-in-Aid for Scientific Research (B) (JSPS KAKENHI no. 23390004, Y.T.), a Grant-in-Aid for JSPS fellows (H.N.) and Meiji Seika Pharma Award in Synthetic Organic Chemistry (Japan) (C.T.).
Abstract
Caprazamycin A has significant antibacterial activity against Mycobacterium tuberculosis (TB). The first total synthesis is herein reported and features a) the scalable preparation of the syn-β-hydroxy amino acid with a thiourea-catalyzed diastereoselective aldol reaction, b) construction of a diazepanone with an unstable fatty-acid side chain, and c) global deprotection with hydrogenation. This report provides a route for the synthesis of related liponucleoside antibiotics with fatty-acid side chains.
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