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标称和实际的总合成

Raphael J Zachmann¹, Kenzo Yahata¹, Mira Holzheimer¹

¹Max-Planck-Institut für Kohlenforschung, 45478 Mülheim/Ruhr, Germany.

Journal of the American Chemical Society

|January 18, 2023

概括

研究人员修改了prorocentin的结构,prorocentin是okadaic酸的自然产品代谢对象. 这项研究使用先进的催化方法澄清了该化合物的核心结构,证实了修订的必要性.

科学领域:

自然产品化学
有机合成
化学生物学

背景情况:

素是一种状聚乙烯,是已知酸抑制剂酸的共代谢物.
一个拟议的生物合成链接和结构相似性表明生物活性的潜在相似性.
之前的研究暗示需要修改prorocentin的分配结构,特别是其核心BCD环系统.

研究的目的:

为了明确prorocentin的正确化学结构.
为了研究 prorocentin 和 okadaic 酸之间的结构关系.
开发一种合成策略,用于访问拟议和修改的前素结构.

主要方法:

采用了灵活的合成蓝图,其中包括晚期黄金催化螺旋循环反应.
关键的转化包括介导的甲基化/转化,黄金催化的替代,和有机催化不对称的 propargylation.
碎片组装涉及Krische化,催化氧化循环和催化不对称的二氧化/氧化.

主要成果:

合成成功地产生了最初提出的和可信的修改后的prorocentin结构.
黄金催化螺旋循环反应选择性地提供了同位素的中央部分.
组装的构件证实了需要修改的prorocentin的既定结构.

结论:

这项研究提供了明确的证据,需要对目前公认的prorocentin结构进行修订.
开发的合成方法为相关的聚乙烯天然产品提供了一种多功能方法.
这项工作解决了结构上的模两可,为未来的生物活性研究奠定了基础.

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