LycogarubinC和LycogalicAcidA的全合成有机化学.pdfVIP

DOI: 10.6023/cjoc201403025 研究论文 有机化学 Chinese Journal of Organic Chemistry ARTICLE Lycogarubin C 和Lycogalic Acid A 的全合成 周妮妮 史 倩 谢志翔* (兰州大学功能有机分子化学国家重点实验室 兰州 730000) 摘要 Lycogarubin C 和 Lycogalic acid A 是用于研究DNA 拓扑异构酶 I (Topo I)抑制剂的重要海洋天然产物. 我们以叔 丁基二甲硅基(TBS)保护的3-丁炔-1 醇为起始原料, 以二甲基 1,2,4,5- 四嗪-3,6-二羧酸酯与炔的杂/逆Diels-Alder 反应为 关键反应, 经 1,2-二嗪还原, Swern 氧化, Fischer 吲哚合成等八步反应实现了Lycogarubin C 的全合成, 再将 Lycogarubin C 以氢氧化钾处理得到Lycogalic acid A. 关键词 Lycogarubin C; Lycogalic acid A; 杂逆 Diels-Alder 反应; Swern 氧化; Fischer 吲哚合成 Total Synthesis of Lycogarubin C and Lycogalic Acid A Zhou, Nini Shi, Qian Xie, Zhixiang* (State Key Laboratory of Applied Organic Chemistry , Lanzhou University, Lanzhou 730000) Abstract Lycogarubin C and lycogalic acid A are key marine natural products which are used in studies on inhibitor of DNA Topoisomerase-I. With (but-3-ynyloxy)(tert-butyl)dimethylsilane as starting material, lycogarubin C was prepared in the process with 8 steps, via hetero-/retro-Diels-Alder reaction, reduction of 1,2-diazine, Swern oxidation, and Fischer indole synthesis as the key reactions, and lycogalic acid A was also obtained in the reaction of lycogarubin C with potassium hydroxide. Keywords lycogarubin C; lycogalic acid A; hetero-/retro-Diels-Alder reaction; Swern oxidation; Fischer indole synthesis 双吲哚生物碱是一类具有重要生物活性的天然产