仿生磷酸盐催化的 Pictet-Spengler 反应合成 1,1'-取代和螺-四氢异喹啉生物碱。
Biomimetic Phosphate-Catalyzed Pictet-Spengler Reaction for the Synthesis of 1,1'-Disubstituted and Spiro-Tetrahydroisoquinoline Alkaloids.
机构信息
Department of Chemistry , University College London , Christopher Ingold Building, 20 Gordon Street , London WC1H 0AJ , U.K.
Department of Biochemical Engineering , University College London , London WC1E 6BT , U.K.
出版信息
J Org Chem. 2019 Jun 21;84(12):7702-7710. doi: 10.1021/acs.joc.9b00527. Epub 2019 May 31.
Tetrahydroisoquinoline (THIQ) alkaloids are an important group of compounds that exhibit a range of bioactivities. Here, a phosphate buffer-catalyzed Pictet-Spengler reaction (PSR) using unreactive ketone substrates is described. A variety of 1,1'-disubstituted and spiro-tetrahydroisoquinoline alkaloids were readily prepared in one-step and high yields, highlighting the general applicability of this approach. This study features the role of phosphate in the aqueous-based PSR and provides an atom-efficient, sustainable route to new THIQs.
四氢异喹啉（THIQ）生物碱是一类重要的化合物，具有多种生物活性。在这里，描述了一种使用非反应性酮底物的磷酸盐缓冲液催化的 Pictet-Spengler 反应（PSR）。各种 1,1'-取代和螺-四氢异喹啉生物碱可以一步高收率地制备，突出了该方法的通用性。本研究探讨了磷酸盐在水相 PSR 中的作用，并提供了一种原子经济、可持续的合成新型 THIQs 的方法。
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