Park Jisook, Chen David Y-K
Department of Chemistry, Seoul National University, Gwanak-1 Gwanak-ro, Gwanak-gu, Seoul, 08826, South Korea.
Angew Chem Int Ed Engl. 2018 Dec 3;57(49):16152-16156. doi: 10.1002/anie.201810974. Epub 2018 Nov 8.
Reported herein is a desymmetrization-based synthetic approach to the fused polycyclic indole alkaloid reserpine. The centerpiece of the developed strategy features an internal desymmetrization process that enabled the use of a readily accessible and nonstereogenic reserpine E-ring precursor, in contrast to the synthesis-intensive and stereodefined E-ring intermediates employed in all past reserpine syntheses. Utilization of inexpensive reagents through an orchestrated sequence of carefully selected chemical transformations further highlight the overall effectiveness of the developed pathway.
本文报道了一种基于去对称化的合成方法来合成稠合多环吲哚生物碱利血平。所开发策略的核心是一个内部去对称化过程，该过程能够使用易于获得的非立体异构的利血平E环前体，这与过去所有利血平合成中使用的合成密集型且立体定义明确的E环中间体形成对比。通过精心选择的一系列化学转化来使用廉价试剂，进一步突出了所开发途径的整体有效性。
