Graduate School of Pharmaceutical Sciences, Chiba University.
Chem Pharm Bull (Tokyo). 2022;70(9):662-668. doi: 10.1248/cpb.c22-00441.
A number of alkaloids found in Mitragyna species belonging to the Rubiaceae family have been shown to have potent biological activity such as analgesic properties. Here, we report the asymmetric total syntheses of mitragynine, speciogynine, and 7-hydroxymitragynine, which are classified as corynantheine-type monoterpenoid indole alkaloids, isolated from Mitragyna speciosa. These syntheses were accomplished within 12 steps and in >11% total yield from commercial 3-(trimethylsilyl)propanal using an organocatalytic anti-selective Michael reaction and bioinspired transformations.
一些在茜草科植物帽蕊木属中发现的生物碱具有很强的生物活性，如具有止痛特性。在这里，我们报告了从 Mitragyna speciosa 中分离出的被归类为帽蕊木型单萜吲哚生物碱的美沙酮、斯皮戈宁和 7-羟基美沙酮的不对称全合成。这些合成是通过使用有机催化的反选择性迈克尔反应和受生物启发的转化，从商业 3-（三甲基甲硅烷基）丙醛出发，经过 12 步反应，以>11%的总收率完成的。
