We have developed a synthesis for tetrahydro‐β‐carbolines involving cascade sigmatropic rearrangements. The substrates were conveniently prepared from parent anilines via a [2,3]‐sigmatropic rearrangement and cyanomethylation. Silver‐mediated decyanation afforded the corresponding iminium cation, which underwent a cascade consisting of an aza‐Cope rearrangement, an aza‐oxa‐Cope rearrangement, an aromatization, and a Pictet–Spengler reaction, and tetrahydro‐β‐carbolines were obtained as the single product. The reaction involved seven bond scissions and four bond formations and was triggered by a single reagent.

中文翻译：

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通过级联正交重排合成四氢 β 咔啉


我们已经开发了一种涉及级联 σ 促性重排的四氢 β 咔啉的合成。底物是通过 [2,3] -sigmatropic 重排和氰甲基化方便地从母体苯胺制备的。银介导的脱氰得到相应的亚胺阳离子，其经历由 aza-Cope 重排、aza-oxa-Cope 重排、芳构化和 Pictet-Spengler 反应组成的级联反应，四氢-β-咔啉作为单一产物获得。该反应涉及 7 个键切割和 4 个键形成，由单一试剂触发。