Issue 9, 2022

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

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

Supplementary files

Article information

Article type
Communication
Submitted
07 Nov 2021
Accepted
30 Nov 2021
First published
01 Dec 2021

Chem. Commun., 2022,58, 1402-1405

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

Y. An, M. Wu, W. Li, Y. Li, Z. Wang, Y. Xue, P. Tang and F. Chen, Chem. Commun., 2022, 58, 1402 DOI: 10.1039/D1CC06278F

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