Among defensive alkaloids isolated from ladybugs, the heterodimeric member chilocorine C possesses an alluring monomeric unit that combines quinolizidine and indolizidine substructures. Indeed, the overall stereochemical disposition of its ring fusions is distinct from related natural products. Herein, we show that a carefully orchestrated sequence with several chemoselective transformations, including a designed cascade that accomplishes 9 distinct chemical reactions in one pot, can smoothly forge that domain and ultimately enable a 15-step, 11-pot enantiospecific synthesis of the natural product. Mechanistic studies, DFT calculations, and the delineation of several other unsuccessful approaches highlight its unique elements.

中文翻译：

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以还原环化/曼尼希反应级联为燃料的 Chilocorine C 的简洁、对映特异性全合成

在从瓢虫中分离出的防御性生物碱中，异二聚体成员 chilocorine C 拥有一个诱人的单体单元，该单元结合了喹尼西啶和吲哚里西啶亚结构。事实上，其环融合体的整体立体化学分布不同于相关的天然产物。在这里，我们展示了一个精心编排的序列与几个化学选择性转化，包括一个设计的级联，在一个锅中完成 9 个不同的化学反应，可以顺利地构建该域，并最终实现天然产物的 15 步、11 锅对映特异性合成. 机理研究、DFT 计算以及其他几种不成功方法的描述突出了其独特的元素。