Total Synthesis of (−)‐Caprazamycin A |
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| Authors: | Hugh Nakamura Dr. Chihiro Tsukano Motohiro Yasui Shinsuke Yokouchi Dr. Masayuki Igarashi Prof. Dr. Yoshiji Takemoto |
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| Affiliation: | 1. Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo‐ku, Kyoto 606‐8501 (Japan);2. Institute of Microbial Chemistry (BIKAKEN), Kamiosaki, Shinagawa‐ku, Tokyo 141‐0021 (Japan) |
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| 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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| Keywords: | aldol reaction antibiotics natural products organocatalysis total synthesis |
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