The total synthesis of <b>(<scp>−</scp>)</b>-strempeliopine <i>via</i> palladium-catalyzed decarboxylative asymmetric allylic alkylation
Yi An, Mengjuan Wu, Weijian Li, Yaling Li, Zhenzhen Wang, Yansong Xue, Pei Tang, Fen‐Er Chen
Abstract
-benzoyl lactam to set up the absolute configuration at the C20 position, a highly diastereoselective one-pot Bischler-Napieralski/lactamization and iminium reduction sequence for the construction of the pentacyclic core structure, and the late-stage dearomative addition of indole, leading to the otherwise difficult-to-achieve hexacyclic indoline framework with complete control of four neighbouring stereocenters.
Topics & Concepts
StereocenterTsuji–Trost reactionTotal synthesisChemistryEnantioselective synthesisIminiumIndolineAllylic rearrangementAlkylationStereochemistryIndole testCatalysisPalladiumCombinatorial chemistryOrganic chemistryAlkaloids: synthesis and pharmacologyChemical synthesis and alkaloidsAdvanced Synthetic Organic Chemistry