异戊烯基化的芳香环结构存在于各类天然产物，这些化合物结构多样，活性涉及药理学各个领域。研究证实，芳香环上异戊烯基的引入增强了分子与生物膜的亲和力，增加了其生物利用度，改善了分子药物代谢和药物动力学。因此，芳香环的异戊烯基化吸引了化学界和药学界广泛的兴趣。本项目将创新性地以大宗的化工原料2-甲基-2-丁烯为异戊烯基试剂，发展吲哚骨架C-2、C-3、C-4、C-7等位的正常及反式脱氢异戊烯基化的高效方法，并将该方法拓展到苯环、呋喃、吡咯等芳香环体系的异戊烯基化。天然产物Versicolamides F-H是一类结构新颖、活性较好的异戊烯基吲哚生物碱。目前，该类生物碱全合成研究未见一例文献报道。本项目拟以自己发展的吲哚C-2位反式异戊烯基化、三组分的不对称缩合反应，有机催化仿生的不对称Diels-Alder反应为关键反应展开Versicolamides F-H及其类似物的不对称全合成研究。

Prenylated armotic rings are found in a broad spectrum of natural products, and the bioactivities of these compounds involve all fields of pharmacology due to a wide array of intriguing architectures. Studies have revealed that the inclusion of the prenyl side chain could enhance both the bioactivity and bioavailability of compounds due to the increased protein binding affinity and membrane permeability caused by the lipophilicity of the prenyl group. Therefore, the prenylation of arenes has received much attention of chemists and pharmacologists. In this project, we proposed to develop efficient prenylations for indole skeleton at special positions (e.g. C-2, C-3, C4, C-7 etc.) with high selectivity of the linear product and the branched product, using a bulk chemical, 2-methyl-2 butene, as prenyl reagent. Also the strategy will be expanded into the prenylations of other aromatic rings, such as benzene, furan, pyrrole and so on. Versicolamides F-H represent a new class of natural prenylated indole alkaloids which have been demonstrated to possess diverse biological activities. To date, there is no reported on the total syntheses of Versicolamides F-H. We plan to carry out asymmetric total syntheses of Versicolamides F-H and analogues with indole C-2 branched prenylation developed by ourselves, asymmetric three-component condensation, organocatalytic biomimetic asymmetric Diels-Alder reaction as key steps.