The total synthesis of (?)-strempeliopine via palladium-catalyzed decarboxylative asymmetric allylic alkylation ?

Chemical Communications Pub Date: 2021-12-01 DOI: 10.1039/D1CC06278F

Abstract

In the work reported herein, the concise and enantioselective total synthesis of the Schizozygine alkaloid (?)-strempeliopine was developed. This synthetic strategy featured the palladium-catalyzed decarboxylative asymmetric allylic alkylation of N-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.

Graphical abstract: The total synthesis of (?)-strempeliopine via palladium-catalyzed decarboxylative asymmetric allylic alkylation
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