松节油合成生物活性角鲨烯反应的研究

Bio-active squalene is a natural chain triterpene whose chemical structure is 2,6,10,15,19,23-hexamethyl-2,6,10,14, 18,22-tetracosane-hexaene that mainly exists in liver oil of sharks. Turpentine oil is a natural monoterpene mixture that is plentiful in China. By the present research, the original idea is realized to synthesize the sea-original squalene from the forest-original turpentine oil, and the synthetic route is comfirmed to be doable. Two key reactions that are the bromination of farnesol and the reduction coupling of the farnesyl bromide were mainly studied in detail. The goal squalene is synthesized by the two key reactions, and analyzed by a capillary GC and GC-MS. The results showed that the synthetic squlene has at least more extra 5 isomers compared with the natural compound (only one isomer) from sea shark's liver oil. Possible structures of the isomers are discossed, and the formation mechanism is predicted as well. The present study that is considered to be a theoretical base for more detailed research and coming use of the synthetic squalene gave a doable synthetic route of sqalene, and it is valuable either for the utilization of plentiful reproducible resource or the protection of the rare resource. By the way, a part of the results of the present study is being studied and developed in a industrial scale in more details as a part of the national tenth five-year project.

角鲨烯是珍稀的天然三十碳六烯，松节油在我国有丰富的资源。根据其特殊结构，本研究大胆提出从松节油合成角鲨烯的独特设想，提出的合成路线十分新颍。主要将从香叶基丙酮合成的橙花叔醇异构成金合欢醇，再变成相应的卤代衍生物，最后偶联得到角鲨烯。同过本研究的开展，将建立松节油合成角鲨烯的路线，具有资源利用和保护的双重价值和意义。