Synthesis Of All-indole Alkaloids TrigonoliiminesA And B

Three indole alkaloids, trigonoliimines A-C, with unprecedented polycyclic skeletons, were isolated from the extract of the leaves of Trigonostemon.lii Y. T. Chang collected inYunnan Province of China by our group. The preliminary activity screening, showed Trigonoliimine A modest anti-HIV activity and inhibition on HBV-DNA replication, but the content of this kind of compounds in plant is very low in the triple gem, and Trigonostemon. lii Y. T. Chang plant resources are very tare, hard to gain this kind of alkaloids from plant directly. So we hope that through economic and simple method for synthesis of Trigonoliimines A, B and its analogues, as module synthesis way of screening drugs.This thesis to indole alkaloids Trigonoliimines A and B of total synthesis as the research object, mainly includes two aspects, the first one is for the lead compounds of Trigonoliimines A and B, that is the dimeric indole synthesis; The second aspect is the comprehensive study on total synthesis of Trigonoliimines A and B, and also carried on some the synthesis of analogues studies.The dimeric indole compounds, not only is we studied Trigonoliimines A and B synthetic precursors, but also many indole alkaloid syntheses of lead compounds and many of the activity of alkaloids are greatly influenced by indoles substituent on. Furthermore, the price of some indoles substituent sales in the market is more expensive. Therefore, this paper on the first hand carried out of the dimeric indole synthesis, hope that through our design line, to find out a simple, can synthesize different substituent dimer method of indole compounds:an idea is introduced into carbonyl in the single indole compounds, again adopt the Fisher indole synthesis to build the second indole to obtained the dimeric indole structure; The second idea is to use two molecules of aldehyde condensation reaction occurs, get a ketone alcohol molecule structure, again through the Fisher indole synthesis method, oxidation of hydroxyl, get the dimeric indole compounds. But, we are first work on the one hand and no breakthrough.The second aspect is to the total synthesis research of Trigonoliimines A and B, is also a key part of this paper. Through structural analysis of compounds, the synthesis methods of design and explore the multiple approaches, and finally to use tryptamine as raw material, through the oxidation reaction, substitution reaction, ammonolysis reaction, Bischler-Napieralski reaction etc. as key step in the reaction, was synthesized successfully demethoxy-trigonoliimine A/B of the six-member ring skeleton structure. During the study at the same time, the synthesis of some nover structure analogue things:demethoxy-trigonoliimines A/B skeleton isomers compounds, demethoxy-trigonoliimines A/B skeleton of bromine compounds. In addition, we also made some analogue design synthesis in this part. Trigonoliimines A/B of the six-member ring skeleton structure and its analogues, and obtain some important research in the process of synthesis intermediates compounds, can be as a pharmacological activity screening of the material basis for the research.