Total Syntheses of (-)-Strictosidine and Related Indole Alkaloid Glycosides.,Angewandte Chemie International Edition

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Total Syntheses of (-)-Strictosidine and Related Indole Alkaloid Glycosides.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-05-04 , DOI: 10.1002/anie.202005748
Jukiya Sakamoto ₁ , Yuhei Umeda ₁ , Kenta Rakumitsu ₁ , Michinori Sumimoto ₂ , Hayato Ishikawa _{1,

3}

Affiliation

A collective synthesis of glycosylated monoterpenoid indole alkaloids is reported. A highly diastereoselective Pictet–Spengler reaction with α‐cyanotryptamine and secologanin tetraacetate as substrates, followed by a reductive decyanation reaction, was developed for the synthesis of (−)‐strictosidine, which is an important intermediate in biosynthesis. This two‐step chemical method was established as an alternative to the biosynthetically employed strictosidine synthase. Furthermore, after carrying out chemical and computational studies, a transition state for induction of diastereoselectivity in our newly discovered Pictet–Spengler reaction is proposed. Having achieved the first enantioselective total synthesis of (−)‐strictosidine in just 10 steps, subsequent bioinspired transformations resulted in the concise total syntheses of (−)‐strictosamide, (−)‐neonaucleoside A, (−)‐cymoside, and (−)‐3α‐dihydrocadambine.

中文翻译：

（-）-Strictosidine和相关的吲哚生物碱糖苷的总合成。

据报道糖基化的单萜类吲哚生物碱的集体合成。开发了一种高度非对映选择性的Pictet-Spengler反应，以α-氰基色胺和secologanin四乙酸酯为底物，然后进行还原性脱氰反应，用于合成（-）-strictosidine，这是生物合成的重要中间体。建立了此两步化学方法，替代了生物合成采用的严格的芥子碱合酶。此外，在进行化学和计算研究之后，提出了在我们新发现的Pictet-Spengler反应中诱导非对映选择性的过渡态。仅用10个步骤就完成了（-）-strictosidine的首次对映选择性全合成，

更新日期：2020-05-04

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