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Synthesis 2024; 56(04): 553-560
DOI: 10.1055/a-2122-4021
DOI: 10.1055/a-2122-4021
special topic
Synthetic Development of Key Intermediates and Active Pharmaceutical Ingredients (APIs)
Construction of an Epoxy-lactone Moiety on the C/D Ring of Highly Oxygenated Triterpenes through a Modified SeO2-Promoted Oxidative Cyclization
The authors gratefully acknowledge financial support from the National Natural Science of Foundation of China (82160744 and 82260683), the Academician Expert Workstation of Yunnan Province (202305AF150030), the Top Young Talent of the Ten Thousand Talents Program of Yunnan Province (to D.L. and L.-D.S.), the Bioactive Ethnopharmacol Molecules Chemical Conversion and Application Innovation Team of the Department of Education of Yunnan Province (2022), and the Start-up Fund of Yunnan University of Chinese Medicine (2019YZG03).
Abstract
We present herein a synthetic endeavor to prepare the epoxy-lactone moiety commonly present in the C/D ring of highly oxygenated triterpenes. Two strategies are applied starting from ursolic acid: (i) Br+-promoted cyclization–isomerization for late-stage epoxidation, and (ii) one-step SeO2-promoted oxidative cyclization. Additionally, the desired epoxy-lactone moiety can be readily prepared on gram scale in one step by using the modified SeO2/TBHP/AcOH oxidative system.
Key words
epoxy-lactone moiety - one-step synthesis - gram-scale - highly oxygenated triterpene - oxidative cyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2122-4021.
- Supporting Information
Publikationsverlauf
Eingereicht: 31. März 2023
Angenommen nach Revision: 03. Juli 2023
Accepted Manuscript online:
04. Juli 2023
Artikel online veröffentlicht:
14. August 2023
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