4.7 Article

Biomimetic Semisynthesis of Arglabin from Parthenolide

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 16, Pages 7103-7107

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo300888s

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Funding

  1. National Natural Science Foundation of China (NSFC) [81001377, 21072106]
  2. Fok Ying Tong Education Foundation [122037]
  3. Natural Science Foundation of Tianjin (TJNSF) [09JCZDJC21900]

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The semisynthesis of arglabin, an anticancer drug in clinical application, is developed from abundant natural product parthenolide via three steps. Each step in this sequence is highly stereoselective, and the substrate-dependent stereoselectivity in the epoxidation step can be explained by computational calculations. The success of chemical semisynthesis of arglabin suggests that the biosynthesis of arglabin might proceed in a similar pathway.

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