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Conformation‐Enabled Total Syntheses of Ohmyungsamycins A and B and Structural Revision of Ohmyungsamycin B |
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| Authors: | Joonseong Hur Dr Jaebong Jang Dr Jaehoon Sim Prof?Dr Woo Sung Son Prof?Dr Hee‐Chul Ahn Dr Tae Sung Kim Yern‐Hyerk Shin Dr Changjin Lim Dr Seungbeom Lee Dr Hongchan An Prof?Dr Seok‐Ho Kim Prof?Dr Dong‐Chan Oh Prof?Dr Eun‐Kyeong Jo Prof?Dr Jichan Jang Prof?Dr Jeeyeon Lee Prof?Dr Young‐Ger Suh |
| Institution: | 1. College of Pharmacy, Seoul National University, Gwanak-gu, Seoul, Republic of Korea;2. College of Pharmacy, CHA University, Pocheon, Gyeonggi-do, Republic of Korea;3. Department of Pharmacy, Dongguk University, Ilsandong-gu, Goyang, Geonggi-do, Republic of Korea;4. Department of Microbiology, Chungnam National University School of Medicine, Jungku, Daejeon, Republic of Korea;5. Natural Products Research Institute, College of Pharmacy, Seoul National University, Gwanak-gu, Seoul, Republic of Korea;6. Division of Applied Life Science, Research Institute of Life Science, Gyeongsang National University, Jinju, Republic of Korea |
| Abstract: | The first total syntheses of the bioactive cyclodepsipeptides ohmyungsamycin A and B are described. Key features of our synthesis include the concise preparation of a linear cyclization precursor that consists of N‐methyl amides and non‐proteinogenic amino acids, and its macrolactamization from a bent conformation. The proposed structure of ohmyungsamycin B was revised based on its synthesis. The cyclic core of the ohmyungsamycins was shown to be responsible for the excellent antituberculosis activity, and ohmyungsamycin variants with truncated chains were evaluated for their biological activity. |
| Keywords: | cyclodepsipeptides macrolactamization natural products structural revision total synthesis |