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布里奥斯塔丁 1,7,9 和 9-N 的总合成₃

Qianyou Guo¹, Yufan Yang¹, Hongyun Zhang¹

¹Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced, Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu, 610041, China.

Angewandte Chemie (International ed. in English)

|January 20, 2025

概括

研究人员实现了多个布里奥斯丁的不同总合成,克服了自然丰度较低的情况. 这一突破为生产这些复杂的海洋天然产品提供了一个可扩展的方法,用于进一步的临床研究.

科学领域:

有机化学有机化学
自然产品合成自然产品合成
药用化学医学化学

背景情况:

布里奥斯塔丁是具有显著治疗潜力的海洋天然产品,超过40个临床试验证明了这一点.
极其低的自然丰度和复杂的结构阻碍了 bryostatins 的研究和开发.
以前的总合成虽然值得注意,但在立体控制,可扩展性和不同的方法方面面临着挑战.

研究的目的:

开发一种强大而不同的合成策略,以获取多种布里奥斯塔丁类似物.
克服自然丰富性的局限性,并使更大规模的生产能够进行进一步的研究.
建立有效和立体选择的方法来构建复杂的布里奥斯塔丁核心结构.

主要方法:

布里奥斯素1,7,9和9-N3的不同总合成.
催化还原性交叉合用于组装关键碎片.
流体化学和可见光诱导的基因对合加法用于融合合成.
内部分子双双 (((silyl) Prins循环转化用于立体选择性B环形成.

主要成果:

取得了成功的布里奥斯素1,7,9和9-N3的分离总合成.
通过精简的最后三个步骤获得了1.5g bryostatin 1的显著产量.
合成路线包括20-22个线性步骤和33-35个总步骤,总产量为3.34.5%.

结论:

开发的合成策略使得能够高效,可扩展地获取多种类型的 bryostatins.
这项工作显著推进了复杂天然产品合成领域.
该方法提供了一个可行的生产布里奥斯塔丁的途径,用于继续进行临床前和临床研究.

关键词:

布里奥斯塔丁类药物是什么?流动化学流动化学王子循环化循环化减速交叉合器的减速交叉合器可见光诱导的基因结合加法.

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