Goto Yuto, Machiya Ayaka, Okumura Taichi, Oka Yusuke, Ito Junya, Ishibashi Osamu, Shiono Yoshihito, Meguro Yasuhiro, Nakagawa Kiyotaka, Kuwahara Shigefumi, Enomoto Masaru
Graduate School of Agricultural Science, Tohoku University, 468-1 Aramaki Aza-Aoba, Aoba-ku, Sendai 980-8572, Japan.
Faculty of Agriculture, Tohoku University, 468-1 Aramaki Aza-Aoba, Aoba-ku, Sendai 980-8572, Japan.
Org Lett. 2025 Aug 1;27(30):8349-8352. doi: 10.1021/acs.orglett.5c02665. Epub 2025 Jul 22.
The synthesis of citrifuran A, a structurally unique natural heterodimer, was accomplished in a bioinspired manner by a thermal [4 + 2] cycloaddition between citrinin and gregatin A, the former of which was synthesized via a Diels-Alder-initiated aromatization reaction and the latter via a Cu-mediated 5- cyclization-bromination as the key steps, respectively. On the other hand, an acid/base-promoted cycloaddition of citrinin with gregatin A followed by hydrolysis of the resulting intermediate furnished citrifuran D.
柠檬呋喃A是一种结构独特的天然杂二聚体，其合成是以仿生方式通过桔霉素与格雷加汀A之间的热[4 + 2]环加成反应实现的。桔霉素是通过狄尔斯-阿尔德引发的芳构化反应合成的，而格雷加汀A则分别通过铜介导的5-环化-溴化反应作为关键步骤合成。另一方面，桔霉素与格雷加汀A在酸碱促进下进行环加成反应，随后对所得中间体进行水解，得到柠檬呋喃D。
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