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Structure units oriented approach towards collective synthesis of sarpagine-ajmaline-koumine type alkaloids

Author

Listed:
  • Wen Chen

    (Yunnan University)

  • Yonghui Ma

    (Yunnan University)

  • Wenyan He

    (Yunnan University)

  • Yinxia Wu

    (Yunnan University)

  • Yuancheng Huang

    (Yunnan University)

  • Yipeng Zhang

    (Yunnan University)

  • Hongchang Tian

    (Yunnan University)

  • Kai Wei

    (Yunnan University)

  • Xiaodong Yang

    (Yunnan University)

  • Hongbin Zhang

    (Yunnan University)

Abstract

Sarpagine-Ajmaline-Koumine type monoterpenoid indole alkaloids represent a fascinating class of natural products with polycyclic and cage-like structures, interesting biological activities, and related biosynthetic origins. Herein we report a unified approach towards the asymmetric synthesis of these three types of alkaloids, leading to a collective synthesis of 14 natural alkaloids. Among them, akuammidine, 19-Z-akuammidine, vincamedine, vincarine, quebrachidine, vincamajine, alstiphylianine J, and dihydrokoumine are accomplished for the first time. Features of our synthesis are a new Mannich-type cyclization to construct the key indole-fused azabicyclo[3.3.1]nonane common intermediate, a SmI2 mediated coupling to fuse the aza-bridged E-ring, stereoselective olefinations to install either the 19-E or 19-Z terminal alkenes presented in the natural alkaloids, and an efficient iodo-induced cyclization to establish the two vicinal all-carbon quaternary centers in the Koumine-type alkaloids.

Suggested Citation

  • Wen Chen & Yonghui Ma & Wenyan He & Yinxia Wu & Yuancheng Huang & Yipeng Zhang & Hongchang Tian & Kai Wei & Xiaodong Yang & Hongbin Zhang, 2022. "Structure units oriented approach towards collective synthesis of sarpagine-ajmaline-koumine type alkaloids," Nature Communications, Nature, vol. 13(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-28535-x
    DOI: 10.1038/s41467-022-28535-x
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    References listed on IDEAS

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    1. Jing Gong & Huan Chen & Xiao-Yu Liu & Zhi-Xiu Wang & Wei Nie & Yong Qin, 2016. "Total synthesis of atropurpuran," Nature Communications, Nature, vol. 7(1), pages 1-6, November.
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    Cited by:

    1. Jun Guo & Di Gao & Jiazhang Lian & Yang Qu, 2024. "De novo biosynthesis of antiarrhythmic alkaloid ajmaline," Nature Communications, Nature, vol. 15(1), pages 1-12, December.

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