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.
J Org Chem. 2021 Apr 16;86(8):6025-6029. doi: 10.1021/acs.joc.1c00390. Epub 2021 Mar 26.
The common, key tricyclic core of stemona alkaloids parvistemonine () and parvistemoline (), whose synthetic efforts have not reported yet, was constructed through a new strategy in which three contiguous stereogenic centers were set by using Carreira's asymmetric Ir/amine-catalyzed allylation of aldehyde with α-vinylfurfuryl alcohol and Ellman's sulfinamide chiral auxiliary, respectively. The furan ring was especially designed to act as the precursor of the butyrolactone while establishing the significant chirality.
具有共同三环基本骨架的斯蒂莫宁型生物碱帕夫斯季莫宁（）和帕夫斯替莫宁（），其全合成尚未见文献报道。我们设计了一条新的合成路线，通过利用 Carreira 的不对称 Ir/胺催化的醛与 α-乙烯基糠醇的烯丙基化反应以及 Ellman 的手性磺酰胺辅助试剂，分别在三个连续的手性中心构建了这个三环基本骨架。呋喃环的设计不仅可以作为构建内酯部分的前体，同时也建立了显著的手性中心。
