State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan, 650091, P. R. China.
Angew Chem Int Ed Engl. 2017 Sep 25;56(40):12327-12331. doi: 10.1002/anie.201707249. Epub 2017 Aug 24.
Outlined herein is a novel and scalable synthesis of (-)-vindorosine based on two key transformations. A highly diastereoselective vinylogous Mannich addition of dioxinone-derived lithium dienolates with indolyl N-tert-butanesulfinyl imines has been developed. In addition, an intramolecular Heathcock/aza-Prins cyclization was introduced to construct both the C, and the highly substituted E rings for the synthesis of (-)-vindorosine and related alkaloids.
本文介绍了一种基于两个关键转化的新型、可扩展的（-）- vindorosine 合成方法。开发了高度非对映选择性的二氧杂环戊酮衍生的锂二烯醇与吲哚基 N-叔丁基亚磺酰亚胺的 vinylogous Mannich 加成反应。此外，还引入了分子内 Heathcock/aza-Prins 环化反应，构建了 C 环和高度取代的 E 环，用于（-）- vindorosine 和相关生物碱的合成。
