Synthetic investigation of lead compounds possessing antitutor and antiviral activities

本课题主要研究了吲哚类生物碱和碳环核苷类化合物中具有应用价值的吲哚基硼酸酯和2-氮杂双环[2.2.1]HEPT-5-en-3-one(ABH)的合成应用。马钱子碱和马钱子碱的串联环化-交叉偶联反应合成马钱子碱的研究2-乙烯基吲哚类化合物的一锅串联环化-交叉偶联反应。通过分子内烷基迁移反应构建咔唑类化合物的新途径，研究了具有亲电中心的吲哚基硼酸酯类化合物的分子内烷基迁移反应，为咔唑类化合物的构建提供了新的方法。利用2-氮杂双环[2.2.1]HEPT-5-en-3-one(ABH)向ABH双键的环加成反应立体选择性地合成了新型碳环核苷衍生物。利用该反应，在碳环核苷衍生物的2‘，3’位与环丙烷、氮杂环丙烷、环氧杂环丙烷等环融合，合成了一种新型碳环核苷。

In this project, the development of synthetic appliobilities of indolylborate and 2-azabicyclo[2.2.1]hept-5-en-3-one (ABH) as a valuable synthon of indole alkaloids and carbocyclic nucleoside derivatives was investigated.1. Synthetic study of strychnos and uleine alkaloids through tandem cyclization-cross-coupling reaction with indolylborateConversion of 2-vinylindole derivatives, readily available from the tandem cyclization-cross-coupling reaction of indolylborate wirh (2-bromoprop-2-enyl)pentyl-3-nylamine in a one-pot manner, to strychnos indole alkaloid was investigated.2. Novel approach to the construction of carbazole derivatives through intramolecular alkyl migration reaction.Investigation of intramolecular alkyl migration reaction in indolylborate possessing an electrophilic center was carried out, which provided novel methodology for the construction of carbazole derivatives.3. Synthesis of novel carbocyclic nucleoside derivatives by the use of 2-azabicyclo[2.2.1]hept-5-en-3-one (ABH)Cycloaddition reaction toward the double bond of ABH proceeded stereoselectively to provide the exo-adduct. This reaction was used for the construction of novel carbocyclic nucleoside fused with cyclopropane, aziridine and oxirane rings at the 2',3' position of carbocyclic nucleoside derivatives.