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生物灵感合成的黄瓜沙米诺 B 和 C 的合成

Mengqing Zhang¹, Jingjing Wu¹

¹Frontiers Science Center for Transformative Molecules, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong University, No. 800, Dongchuan Road, Shanghai, 200240, China.

Angewandte Chemie (International ed. in English)

|November 6, 2024

概括

研究人员首次合成了cucurbalsaminones B和C,这些天然产品具有强大的反转多药耐药活性. 这种来自兰醇的14步合成利用了新的仿生和生物灵感重组.

科学领域:

有机化学有机化学
自然产品的合成自然产品的合成
药用化学医学化学

背景情况:

库库尔巴萨米诺 B 和 C 是阿贝奥-库库尔比坦三类.
这些化合物具有独特的化环系统.
它们表现出显著的反转多药耐药性 (MDR) 活性.

研究的目的:

报告第一个库库尔巴萨米诺 B 和 C 的总合成.
开发一个高效的合成路由,从易于获得的原料.

主要方法:

一个14步合成策略,从兰醇开始.
使用仿生瓦格纳-米尔韦恩重新排列来构建骨.
采用生物启发的光化学氧化二甲 (ODPM) 重组.
整合了Eosin Y光诱导的巴顿-麦康比脱氧,以调整C11的氧化状态.

主要成果:

成功合成了B和C型库库尔巴胺氨基.
证明了构建复杂的5/6/3/6/5合环系统的可行性.
解决了修改硬质阻碍的C11位置的挑战.

结论:

开发的合成路线可以获得有价值的自然产品.
合成方法展示了重新排列反应的创新应用.
这项工作为进一步探索用于药物应用的库库尔巴萨米诺类 analog铺平了道路.

关键词:

生物灵感合成的合成黄瓜类氨基的氨基.库库尔比坦三基化物光化学氧化二甲 (ODPM) 的重新排列.照片诱导的巴顿 - 麦康比脱氧.

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