Issue 6, 2023

Stereoselective semisynthesis of uzarigenin and allo-uzarigenin

Abstract

Herein, we report the concise semisynthesis of the natural cardenolide uzarigenin and its diastereoisomer allo-uzarigenin in nine and seven steps, respectively, starting from the broadly available epi-androsterone. For this purpose, the synthetic strategy for the stereoselective introduction of the β-hydroxy group at C-14 via Mukaiyama oxidation is discussed. Additionally, the installation of the butenolide ring at C-17 is performed using a Stille-cross-coupling reaction with subsequent stereoselective hydrogenation of the C-16/C-17 double bond to exclusively give allo-uzarigenin. By directing the hydrogenation via a protecting group strategy, the C-17β isomer can also be obtained stereoselectively.

Graphical abstract: Stereoselective semisynthesis of uzarigenin and allo-uzarigenin

Supplementary files

Article information

Article type
Research Article
Submitted
28 out 2022
Accepted
24 dez 2022
First published
09 jan 2023
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2023,10, 1435-1440

Stereoselective semisynthesis of uzarigenin and allo-uzarigenin

S. Al Muthafer, C. Schissler, V. Koch, H. Kühner, M. Nieger and S. Bräse, Org. Chem. Front., 2023, 10, 1435 DOI: 10.1039/D2QO01718K

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