Kim Cheoljae, Kang Soyeong, Rhee Young Ho
Department of Chemistry, POSTECH , 77 Cheongam-Ro, Nam-Gu, Pohang, Kyungbuk, Republic of Korea , 790-784.
J Org Chem. 2014 Nov 21;79(22):11119-24. doi: 10.1021/jo502103p. Epub 2014 Nov 3.
An efficient synthesis of the tricyclic cyclopenta[1,2-b]pyrrolo[1,2-a]azepine nucleus of stemonamine alkaloids is reported. The key reaction utilizes a one-pot gold(I)-catalyzed cyclization and SnCl4-mediated Schmidt rearrangement. Notably, the phosphine ligand had a crucial effect on the gold(I)-catalyzed cyclization. As an application of this new methodology, the formal synthesis of (±)-stemonamine has been accomplished.
报道了百部碱生物碱三环环戊并[1,2 - b]吡咯并[1,2 - a]氮杂䓬核的高效合成方法。关键反应采用一锅法金（I）催化环化和四氯化锡介导的施密特重排反应。值得注意的是，膦配体对金（I）催化的环化反应有至关重要的影响。作为这种新方法的应用，已完成了（±） - 百部碱的形式合成。
