Total Synthesis of (−)-Gardmultimine A

作者：Peiqi Chen, Hesi Yang, Hao Zhang, Wei Chen, Zheng Zhang, Jing Zhang, Huilin Li, Xiaolei Wang, Xingang Xie, Xuegong She · 发表于：Organic Letters · 年份：2020 · DOI：10.1021/acs.orglett.0c00399 · 被引用次数：32 · 研究领域：Catalytic C–H Functionalization Methods、Alkaloids: synthesis and pharmacology、Marine Sponges and Natural Products

The first total synthesis of Gardneria oxindole alkaloid (−)-gardmultimine A has been achieved in 19 steps from d -tryptophan in a fully stereocontrolled manner. This synthesis features (1) an Ir-catalyzed regioselective C–H borylation/oxidation sequence to introduce the C12 methoxyl group, (2) a stereocontrolled oxidative rearrangement of indole to construct the spirooxindole motif, and (3) an Au(I)-catalyzed transannular Conia-ene-type 6-exo-dig cyclization to establish the azabicyclo[2.2.2]octane skeleton and the exocyclic E -alkene with exclusive stereoselectivity.