Total Synthesis of (+)-Shearilicine

作者：Daria E. Kim, Yingchuan Zhu, Shingo Harada, Isaiah Aguilar, Abbigayle E. Cuomo, Minghao Wang, Timothy R. Newhouse · 发表于：Journal of the American Chemical Society · 年份：2023 · DOI：10.1021/jacs.2c13584 · 被引用次数：21 · 研究领域：Advanced Synthetic Organic Chemistry、Alkaloids: synthesis and pharmacology、Plant-based Medicinal Research

Herein we report the first total synthesis of the indole diterpenoid natural product shearilicine by an 11-step sequence via a generalizable precursor to the highly oxidized subclass of indole diterpenoids. A native chiral auxiliary strategy was employed to access the target molecule in an enantiospecific fashion. The formation of the key carbazole substructure was achieved through a mild intramolecular Heck cyclization, wherein a computational study revealed noncovalent substrate-ligand and ligand-ligand interactions that promoted migratory insertion.