【作者】 田靖靖；

【导师】 韩丙；

【作者基本信息】 兰州大学 ， 有机化学， 2015， 博士

【摘要】 本论文主要对吲哚生物碱subincanadine E, anominine以及咔唑生物碱tubingensin A的全合成经行了研究,主要包括两部分的内容：第一章、Subincanadine E的全合成研究Subincanadines系列化合物是由日本科学家Kobayashi,从巴西的药用植物Aspidosperma subincanum Mart中分离得到的,其中subincanadine E又名pericine,最早是由Stockigt教授于1982年从Picralima nitida细胞培养液中分离得到的,对于小鼠的淋巴癌细胞及人类的皮肤癌细胞具有一定的抗癌活性。本章简要介绍了subincanadines系列化合物的合成现状。对subincanadine E的全合成进行了探索研究,最终,从色胺盐酸盐出发,以Ni(COD)2作用下的Micheal加成反应及锌作用下的碎裂化反应为关键步,首次完成了subincanadine E的全合成。第二章、Anominine以及Tubingensin A的合成研究二萜生物碱anominine及咔唑生物碱tubingensin A是由美国科学家Gloer教授于1989年从曲霉菌菌核提取液中分离出来的,具有杀虫,抗病毒的活性。本章对anominine及tubingensin A的以往合成经行了简要的总结。对anominine及tubingensin A的合成,依次尝试了以炔炔环化、烯炔环化反应,分子间Diels-Alder反应,分子内Friedel-Crafts烷基化为关键步的三条不同策略。更多还原

【Abstract】 This thesis mainly focuses on synthetic studies of indole alkaloid subincanadine E, aominine and carbazole alkaloids tubingensin A, which includes the following two parts:Chapter 1:Total synthesis of (±)-subincanadine E.Natural products subincanadines were isolated from the bark of the Brazilian medicinal plant Aspidosperma subincanum Mart by Kobayashi and co-workers. Among these products, subincanadine E, also named pericine, was first isolated from Picralima nitida cell suspension cultures by Joachim Stockigt in 1982. Subincanadine E was found to have cytotoxicity against murine lymphoma L1210 cells and human epidermoid carcinoma KB cells based on in vitro preliminary biological experiments. In this chapter, the previous synthetic studies toward subincanadines have been reviewed briefly. Subsequently, the first total synthesis of subincanadine E was described, which commenced from tryptamine hydrochloride salt and key features included Ni(COD)2-mediated intramolecular Michael addition and zinc-mediated fragmentation reaction.Chapter 2:Synthetic studies of aominine and tubingensin A.Indole diterpenoid anomine and carbazole alkaloid tubingensin A were isolated from the sclerotia of the fungus by Gloer in1989, and display insecticidal and antiviral activity. In this chapter, the previous synthetic studies toward anomine and tubingensin A have been reviewed briefly. Then our synthetic approach for the total synthesis about tubingensin A and anomine were described, which incloud three different routes with enyne cyclization or diyne cyclization, intermolecular Diels-Alder reaction and intramolecular Friedel-Crafts alkylation as key steps respectively.更多还原