Icyishaka Philippe, Li Chenxing, Lu Liushen, Bao Wenhao, Li Jia, Zhang Yan, Rao Yijian
Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University.
School of Pharmaceutical Science, Jiangnan University.
J Vis Exp. 2020 Jul 17(161). doi: 10.3791/60786.
The interest on nitrogen-containing heterocycles has expanded rapidly in the synthetic community since they are important motifs for new drugs. Traditionally, they were synthesized through thermal cycloaddition reactions, whereas today, photocatalysis is preferred due to the mild and efficient conditions. With this focus, a new photocatalytic method for the synthesis of nitrogen-containing heterocycles is highly desired. Here, we report a protocol for the biosynthesis of cercosporin, which could function as a metal-free photocatalyst. We then illustrate cercosporin-photocatalyzed protocols for the synthesis of nitrogen-containing heterocycles 1,2,3-thiadiazoles through annulation of azoalkenes with KSCN, and synthesis of 1,4,5,6-tetrahydropyridazines [4+2] through cyclodimerization of azoalkenes under mild conditions, respectively. As a result, there is a new bridge between the microbial fermentation method and organic synthesis in a mild, cost-effective, environmentally friendly and sustainable manner.
含氮杂环在合成领域的关注度迅速增长，因为它们是新药的重要结构单元。传统上，它们是通过热环加成反应合成的，而如今，由于条件温和且高效，光催化合成法更受青睐。基于此，人们迫切需要一种用于合成含氮杂环的新型光催化方法。在此，我们报道了一种环孢菌素生物合成的方案，该方案中，环孢菌素可作为无金属光催化剂。然后，我们分别阐述了通过偶氮烯烃与硫氰酸钾环化反应光催化合成含氮杂环1,2,3-噻二唑，以及在温和条件下通过偶氮烯烃环二聚反应光催化合成1,4,5,6-四氢哒嗪[4+2]的方案。结果，以温和、经济高效、环境友好且可持续的方式在微生物发酵法与有机合成之间搭建了一座新的桥梁。
