中文摘要：

LycogarubinC和lycogalicacid是南Steglich和Akazawa在1994年分别独立从粘细菌Lycogalaepidendrum中分离得到的海洋天然产物．LycogarubinC有-定的细胞毒活性；lycogalicacid是螺旋-环-螺旋（Helix—Loop—Helix，bHLH）翻译阻遏因子HesI=聚体的抑制剂．另外，lycogalicacid是吲哚[2，3．口]咔唑类生物碱的生物合成的关键中间体，吲哚[2，3-口]咔唑类生物碱有广泛的生物活性．本文报道了两条合成lycogarubinC和lycogalicacid的路线．路线-：由吲哚和吡咯出发经过8步反应以27％的收率得到lycogarubinC，其中的关键步骤是3,4-二碘-1H-III：L咯-2，5-二甲酸甲酯和N-对甲基苯磺酰基-1似吲哚-3-硼酸的Suzuki—Miyaura交叉偶联反应；路线二：由亚氨基二乙酸出发经过7步反应以25％的收率得到lycogarubinC，其中的关键步骤是N-苄基亚氨基二乙酸二甲酯和草酸二甲酯的Hinsberg反应和3,4-二二氟甲磺酸氧基-1H-@咯．2，5．二甲酸甲酯和Ⅳ．二甲基叔丁基硅基．1＊吲哚．3．硼酸的钯催化的交叉偶联反应．LycogarubinC再经水解之后酸化得到lycogalicacid．细胞毒实验表明lycogarubinC对MDA—MB-231，A549，HeLa和PC3肿瘤细胞有一定的生长抑制作用，进一步研究表明它具有DNA拓扑异构酶2的抑制活性．

英文摘要：

Lycogarubin C and lycogalic acid were first isolated independently by Steglich and Akazawa from Lycogala epidendrum in 1994. Lycogarubin C showed a potential cytotoxic activity. Lycogalic acid is an inhibitor of Hesl dimmer of helix-loop-helix （bHLH） transcriptional repressor factor. Lycogalic acid is also the key intermediate in the biosynthesis of indolo[2,3-a]carbazole alkaloids that exhibit broad spectrum of bioactivity. Two efficient synthetic pathways of lycogarubin C and lycogalic acid were completed in this study. The first pathway included eight steps started from the commercially avail- able indole and pyrrole to produce lycogarubin C with an overall yield of 27%. The second pathway was completed in seven steps with an overall yield of 25%. The key reactions are palladium-catalyzed Suzuki-Miyaura coupling of bis-iodo or bis-triflate derivative and indolboronic acid derivatives and Hinsberg-type synthesis of dimethyl N-benzyl-3,4- dihydroxypyr- role-2,5-dicarboxylate, respectively. Treatment of lycogarubin C with sodium hydroxide in ethanol under refluxing followed by acidification afforded lycogalic acid quantitatively. Lycogarubin C and lycogalic acid showed the antiproliferative activities against four human tumor cell lines of MDA-MB-231, A549, HeLa and PC3. Further study showed that lycogarubin C inhib- ited the activity of DNA topoisomerase 2.