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 10 2022
Accepted
24 12 2022
First published
09 1 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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