State Key Laboratory of Phytochemistry and Plant Resources in West China , Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201 , China.
University of Chinese Academy of Sciences , Beijing 100049 , China.
Org Lett. 2019 Oct 18;21(20):8485-8487. doi: 10.1021/acs.orglett.9b03319. Epub 2019 Oct 9.
A catalytic, enantioselective formal synthesis of monoterpene indole alkaloid (-)-alstoscholarine is described. The synthesis employs an Ir-amine dual catalyzed asymmetric allylation of aldehyde with 3-indolyl vinyl carbinol derivative to furnish chiral aldehyde as a key asymmetric step. Other key reactions include the construction of the 2-ketopyrrole moiety by Nicolaou's method and TfO promoted Pictet-Spengler cyclization to access Zhu's intermediate .
描述了一种催化、对映选择性的单萜吲哚生物碱（-）-阿替生碱的形式合成。该合成采用 Ir-胺双催化不对称烯丙基化醛[1]与 3-吲哚基乙烯基甲醇衍生物[2]，以提供手性醛[3]作为关键的不对称步骤。其他关键反应包括通过 Nicolaou 方法构建 2-酮吡咯部分和 TfO 促进的 Pictet-Spengler 环化以获得朱的中间体[4]。
