A Formal Synthesis of (±)-Arborisidine

作者：Liang Huo, Yunxia Yang, Xiaofei Gao, Wei Chen, Xuegong She, Xiao‐Ping Cao · 发表于：Organic Letters · 年份：2024 · DOI：10.1021/acs.orglett.4c00928 · 被引用次数：10 · 研究领域：Chemical synthesis and alkaloids、Synthetic Organic Chemistry Methods、Advanced Synthetic Organic Chemistry

Herein, we report a formal synthesis of (±)-arborisidine via the creation of Jiao's intermediate with the critical caged structure. Starting from tryptamine, a Pictet-Spengler cyclization forged the piperidine ring, a Pd-catalyzed indole allylation and ring-closing metathesis protocol afforded a bridged aza-bicyclo[3.3.1]nonane moiety, and an intramolecular N-alkylation closed the final pyrrolidine ring. This study provides a new approach to the unique caged framework of arborisidine and relevant alkaloids.