不对称全合成五环吲哚生物碱安纳吉宁和从 Kopsia arborea 中分离得到的天然产物的绝对构型。

Asymmetric Total Synthesis of Pentacyclic Indole Alkaloid Andranginine and Absolute Configuration of Natural Product Isolated from Kopsia arborea.

机构信息

Graduate School of Pharmaceutical Sciences, Chiba University , 1-8-1 Inohana, Chuo-ku, Chiba 260-8675, Japan.

出版信息

Org Lett. 2017 May 19;19(10):2722-2725. doi: 10.1021/acs.orglett.7b01076. Epub 2017 May 8.

DOI:10.1021/acs.orglett.7b01076

Abstract

The first asymmetric total synthesis of andranginine (1) via an asymmetric Morita-Baylis-Hillman reaction and a diastereoselective intramolecular Diels-Alder reaction has revealed that natural andranginine (1) isolated from Kopsia arborea existed as a scalemic mixture and contained predominantly the (16R,21S) form rather than the (16S,21R) form.

摘要

通过不对称的 Morita-Baylis-Hillman 反应和立体选择性的分子内 Diels-Alder 反应，首次实现了对 (+)-安格洛宁碱（1）的不对称全合成，这表明从 Kopsia arborea 中分离得到的天然 (+)-安格洛宁碱（1）以外消旋混合物的形式存在，并且主要含有（16R,21S）构型，而不是（16S,21R）构型。