咔唑生物碱 Tubingensin A 是由美国科学家Gloer教授及其合作者于1989年从曲霉菌菌核的正己烷提取液中分离得到的，它展现了良好的生理活性，不仅具有较强的抗棉铃虫活性，而且对单纯性疱疹病毒也具有较好的抗病毒活性（IC50 = 8 μg/mL）。Tubingensin A 的结构具有一个极其新颖的顺式的十氢萘并咔唑的核心骨架，一个手性中心密集的六元环，共含有四个立体中心，其中包含两个连续全碳季碳立体中心。由于其新颖而复杂的结构和独特的生理活性，吸引了很多课题组对 Tubingensin A 及其相关生物碱展开合成研究，但迄今仅有两篇有关其全合成工作的报道。为建立高效的合成方法并获取足够量天然产物为今后进一步生物学研究打下基础，我们希望以[3+2]环加成和串联的Wagner-Meerwein重排/芳构化作为关键步来完成Tubingensin A 新颖的全合成。

Carbazole alkaloid tubingensin A, first isolated from the sclerotia of the fungus by Gloer and co-workers in1989, has been found to be bioactive against the widespread crop pest Heliothis zea and the herpes simplex virus type 1 （IC50 = 8 μg/mL）. Structurally, tubingensin A possesses a disubstituted carbazole fused to a densely functionalized cis-decalin framework. Moreover, the decalin core contains four contiguous stereocenters, two of which are vicinal quaternary carbon centers. The remarkable structural features of tubingensin A, coupled with its notable bioactivities, have rendered it an attractive target molecule for the synthetic community. However, there have been only two total syntheses reported so far. We wish to develop a new efficient synthetic approach to tubingensin A and its derivatives featuring Wagner-Meerwein rearrangement and [3+2] cycloaddition as the key transfromations, with which new and relevant compounds useful for innovative vermifuge studies would be hopefully provided.