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Stereoselective Synthesis of Maralixibat via VO(acac)2/Schiff Base-Catalyzed Asymmetric Oxidation of Its Sulfide
Ziyu Peng1, Mercy Mpofo1, Zheng Jie1
1School of Chemistry and Chemical Engineering, Wuhan University of Science and Technology, Wuhan, Hubei Province, P. R. China 430081.
Abstract:
The stereoselective synthesis of maralixibat was achieved by harnessing the chiral transferring effect of the stereogenic R-sulfoxide functionality, which was obtained via the VO(acac)2/Schiff base-catalyzed asymmetric oxidation of a phenylthiophenol prochiral intermediate. The R-sulfoxide intermediate underwent a ring closure reaction to form the seven-membered ring core structure with the desired stereochemistry, ultimately ensuring the drug's exceptional isomeric purity and synthetic efficiency.
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