Cao Mingyu, Wang Yiming, Zhang Yong, Zhang Caiyun, Chen Niangen, Zhang Xiaopo
Key Laboratory of Tropical Translational Medicine of Ministry of Education, Hainan Key Laboratory for Research and Development of Tropical Herbs, School of Pharmacy, Hainan Medical University, Haikou 571199, China.
Research Center for Drug Safety Evaluation of Hainan Province, Hainan Medical University, Haikou 571101, China.
Molecules. 2024 Feb 5;29(3):745. doi: 10.3390/molecules29030745.
The total synthesis of laurolitsine was achieved for the first time. This reaction was accomplished in 14 steps with a 2.3% yield (this was calculated using 3-hydroxy-4-methoxybenzaldehyde as the starting material) starting from two simple materials, 3-hydroxy-4-methoxybenzaldehyde and 2-(3-hydroxy-4-methoxyphenyl)acetic acid, and the longest linear sequence consisted of 11 steps. The key steps included an electrophilic addition reaction in which a nitro group was reduced to an amino group using lithium tetrahydroaluminum and a Pd-catalyzed direct biaryl coupling reaction. In this paper, many of the experimental steps were optimized, and an innovative postprocessing method in which 2-(3-(benzyloxy)-4-methoxyphenyl)ethanamine is salted with oxalic acid was proposed.
首次实现了月桂番荔枝碱的全合成。该反应从两种简单原料3-羟基-4-甲氧基苯甲醛和2-(3-羟基-4-甲氧基苯基)乙酸开始，以14步完成，产率为2.3%（以3-羟基-4-甲氧基苯甲醛为起始原料计算），最长线性序列由11步组成。关键步骤包括亲电加成反应，其中使用四氢铝锂将硝基还原为氨基以及钯催化的直接联芳基偶联反应。本文对许多实验步骤进行了优化，并提出了一种创新的后处理方法，即用草酸使2-(3-(苄氧基)-4-甲氧基苯基)乙胺成盐。
