Stereoselective synthesis of an eleganine A core.,Organic & Biomolecular Chemistry

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Stereoselective synthesis of an eleganine A core.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-06-04 , DOI: 10.1039/d0ob00939c
Gints Smits ₁ , Ronalds Zemribo ₁

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A synthetic approach towards the core of a structurally unique cytotoxic indole alkaloid eleganine A has been accomplished for the first time. The synthesis features a stereoselective Ireland–Claisen rearrangement as the key step, enabling the installation of 2 stereogenic centers and a stereodefined double bond in a single step. Furthermore, a SnCl₄ promoted acylation of the indole C-2 position allows the coupling of a highly functionalized 4-ethylidene proline fragment with the indole part.

中文翻译：

eleganine A核心的立体选择性合成。

首次完成了针对结构独特的细胞毒性吲哚生物碱线虫氨酸A核心的合成方法。该合成的关键步骤是将爱尔兰-克莱森立体选择性重排作为关键步骤，从而使一步即可安装2个立体异构中心和一个立体定义的双键。此外，SnCl ₄促进的吲哚C-2位置的酰化作用使高度官能化的4-亚乙基脯氨酸片段与吲哚部分偶联。

更新日期：2020-06-24

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