分子内力
全合成
立体化学
化学
吡那考
酮
戒指(化学)
组合化学
序列(生物学)
萘醌
有机化学
催化作用
生物化学
作者
Shunichi Kusumi,Harunobu Nakayama,Takumi Kobayashi,Hajime Kuriki,Yuka Matsumoto,Daisuke Takahashi,Kazunobu Toshima
标识
DOI:10.1002/chem.201604697
摘要
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.
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