Iodospirocyclization of Tryptamine‐Derived Isocyanides: Formal Total Synthesis of Aspidofractinine,Angewandte Chemie International Edition

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Iodospirocyclization of Tryptamine‐Derived Isocyanides: Formal Total Synthesis of Aspidofractinine
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2018-10-17 , DOI: 10.1002/anie.201809678
Jordy M. Saya ₁ , Thomas R. Roose ₁ , Jarryt J. Peek ₁ , Bram Weijers ₁ , Thomas J. S. de Waal ₁ , Christophe M. L. Vande Velde ₂ , Romano V. A. Orru ₁ , Eelco Ruijter ₁

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The N‐iodosuccinimide‐mediated spirocyclization of tryptamine‐derived isocyanides to generate spiroindolenines is reported. The products contain both an imine and an imidoyl iodide as flexible handles for follow‐up chemistry. Nucleophilic addition typically occurs chemoselectively on the imine moiety with complete diastereoselectivity, providing opportunities for the construction of complex molecular frameworks. The synthetic potential of the method was showcased in the formal total synthesis of (±)‐aspidofractinine.

中文翻译：

色胺胺衍生的异氰化物的碘螺环化：Aspidofractinine的正式全合成

据报道，N-碘丁二酰亚胺介导的色胺的异氰酸酯的螺环化反应可生成螺吲哚烯。该产品同时包含亚胺和亚氨基碘化物，可作为后续化学反应的灵活处理方法。亲核加成通常在亚胺部分上以化学选择性发生，具有完全的非对映选择性，为构建复杂的分子框架提供了机会。该方法的合成潜力在（±）-aspidofractinine的正式总合成中得到了证明。

更新日期：2018-10-17

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