Issue 5, 2024

Enantioselective total syntheses of (−)-mitragynine, (−)-quinine and (+)-quinidine enabled by Ir-catalysed asymmetric hydrogenation of all-carbon tetrasubstituted cycloalkenes

Abstract

Enantioselective total syntheses of three alkaloids (−)-mitragynine, (−)-quinine and (+)-quinidine are reported. These syntheses rely on an Ir-catalysed asymmetric hydrogenation of tetrasubstituted α-acylpyrazole-β-alkyl cycloalkenes to construct piperidine rings bearing 1,2-contiguous cis-stereocenters in high yields (90% and 97%) with excellent enantioselectivities (93% and 96% ee).

Graphical abstract: Enantioselective total syntheses of (−)-mitragynine, (−)-quinine and (+)-quinidine enabled by Ir-catalysed asymmetric hydrogenation of all-carbon tetrasubstituted cycloalkenes

Supplementary files

Article information

Article type
Research Article
Submitted
09 Dec 2023
Accepted
15 Jan 2024
First published
17 Jan 2024

Org. Chem. Front., 2024,11, 1456-1461

Enantioselective total syntheses of (−)-mitragynine, (−)-quinine and (+)-quinidine enabled by Ir-catalysed asymmetric hydrogenation of all-carbon tetrasubstituted cycloalkenes

K. Zhang, P. Cui, M. Miao, M. Zeng, X. Wang, M. Zhang, Q. Chen, H. Song, B. Ke and Y. Qin, Org. Chem. Front., 2024, 11, 1456 DOI: 10.1039/D3QO02034G

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