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Total Synthesis of Aquayamycin |
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| Authors: | Shunichi Kusumi Harunobu Nakayama Takumi Kobayashi Hajime Kuriki Yuka Matsumoto Prof?Dr Daisuke Takahashi Prof?Dr Kazunobu Toshima |
| Institution: | Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan |
| Abstract: | An efficient and practical total synthesis of aquayamycin has been accomplished. The highly oxidized and stereochemically complex tetracyclic ring system was constructed using three key reactions: 1) highly diastereoselective 1,2‐addition of C‐glycosyl naphthyllithium to a cyclic ketone, 2) indium‐mediated site‐selective allylation‐rearrangement sequence of naphthoquinone, and 3) diastereoselective intramolecular pinacol coupling. This synthetic strategy offers a novel and efficient pathway to prepare aquayamycin‐type angucycline antibiotics. |
| Keywords: | angucycline antibiotics antitumor antibiotics aquayamycin natural products total synthesis |