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Site-selective C-H hydroxylation of pentacyclic triterpenoids directed by transient chiral pyridine-imino groups

Author

Listed:
  • Tong Mu

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Bingcheng Wei

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Dapeng Zhu

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Biao Yu

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

Abstract

Pentacyclic triterpenoids (PTs) constitute one of the biggest families of natural products, many with higher oxidation state at the D/E rings possess a wide spectrum of biological activties but are poorly accessible. Here we report a site-selective C-H hydroxylation at the D/E rings of PTs paving a way toward these important natural products. We find that Schönecker and Baran’s Cu-mediated aerobic oxidation can be applied and become site-selective on PT skeletons, as being effected unexpectedly by the chirality of the transient pyridine-imino directing groups. To prove the applicability, starting from the most abundant triterpenoid feedstock oleanane, three representative saponins bearing hydroxyl groups at C16 or C22 are expeditiously synthesized, and barringtogenol C which bears hydroxyl groups at C16, C21, and C22 is synthesized via a sequential hydroxylation as the key steps.

Suggested Citation

  • Tong Mu & Bingcheng Wei & Dapeng Zhu & Biao Yu, 2020. "Site-selective C-H hydroxylation of pentacyclic triterpenoids directed by transient chiral pyridine-imino groups," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-18138-9
    DOI: 10.1038/s41467-020-18138-9
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