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Synthesis of α,β-Unsaturated Ketones from Natural Triterpenoids and Sterol by IBX Mediated Oxidation

  • Yu-jiao Liu
  • Guo-li Huang
  • Hao-liang Li
  • Ye-gao ChenEmail author
Article

α,β-Unsaturated ketones have attracted much attention as some compounds showed remarkable bioactivities [1, 2, 3]. However, not many of these compounds exist in nature, whereas structures containing hydroxyl groups are abundant [4]; they provide an interesting entry point for chemical transformation to α,β-unsaturated ketones. The aim of this work is to study o-iodoxybenzoic acid (IBX) mediated oxidation, an efficient and user-friendly procedure for the oxidation of alcohols to α,β-unsaturated ketones [5, 6]. Two natural triterpenoids 20(R)-panaxatriol and taraxerol, previously isolated from Panax notoginseng and Pterospermum yunnanense [7], and one sterol β-sitosterol, were used as substrates. The reaction results in the formation of α,β-unsaturated ketones from the natural products used.

To a solution of the substrate (0.1–1.2 mmol) in DMSO–toluene (4:1, 5 mL) was added IBX (0.3–3.0 mmol) in one portion. The mixture was heated to 85°C, followed by TLC until no starting material was...

Notes

Acknowledgment

The work was supported by the Key Laboratory (No. 2016-5) and Science and Technology Innovation Team of Higher Education (No. 2014-6) in Yunnan, China.

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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Yu-jiao Liu
    • 1
  • Guo-li Huang
    • 1
  • Hao-liang Li
    • 1
  • Ye-gao Chen
    • 1
    Email author
  1. 1.School of Chemistry and Chemical EngineeringYunnan Normal UniversityKunmingP. R. China

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