Enantioselective Total Synthesis and Absolute Configuration Assignment of (+)-Tronocarpine by an Asymmetric Michael/Aldol Reaction

We present die first asymmetrictotalsyntfiesis and iû>solute configuration tletermination of (+)-tnmocarpine, The [6.5.7.6.6] pentacyctic core was constructed at an early stage by using a sequential cyclization strategy Omnigfi a newly developed analytic asymmetric Michaei/aklol cascade to build die azu[3.3.1]-bridged cycle and a ttuidem reduction/fiemiamidation procedure to assemble tfie seven-m embered lactam The side-chain functionalities were incorporated at a late stage by several appropriately orchestrated manipulations under mild conditions The synthesis of enantiomerically pure (+)-tronocorpine was achieved through a 20-step longest linear sequence from trypiamine. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.