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Gram-Scale Synthesis of the C14–C23 Fragment of Eribulin

  • Qiuhan Yu
    Qiuhan Yu
    Department of Medicinal Chemistry School of Pharmacy, China Pharmaceutical University, 639 Longmian Avenue, Nanjing, Jiangsu 211198, P. R. of China
    More by Qiuhan Yu
  • Yueer Zhou
    Yueer Zhou
    Department of Medicinal Chemistry School of Pharmacy, China Pharmaceutical University, 639 Longmian Avenue, Nanjing, Jiangsu 211198, P. R. of China
    More by Yueer Zhou
  • Xinai Gao
    Xinai Gao
    Department of Medicinal Chemistry School of Pharmacy, China Pharmaceutical University, 639 Longmian Avenue, Nanjing, Jiangsu 211198, P. R. of China
    More by Xinai Gao
  • Shuheng Pan
    Shuheng Pan
    Department of Medicinal Chemistry School of Pharmacy, China Pharmaceutical University, 639 Longmian Avenue, Nanjing, Jiangsu 211198, P. R. of China
    More by Shuheng Pan
  • Feng Lin*
    Feng Lin
    WuXi AppTec, 288 Fute Zhong Road, Waigaoqiao Free Trade Zone, Shanghai 200131, P. R. of China
    *Email: [email protected]
    More by Feng Lin
  • , and 
  • Wei Li*
    Wei Li
    Department of Medicinal Chemistry School of Pharmacy, China Pharmaceutical University, 639 Longmian Avenue, Nanjing, Jiangsu 211198, P. R. of China
    *Email: [email protected]
    More by Wei Li
Cite this: Org. Process Res. Dev. 2023, 27, 2, 367–372
Publication Date (Web):February 6, 2023
https://doi.org/10.1021/acs.oprd.2c00370
Copyright © 2023 American Chemical Society

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    Abstract

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    Eribulin is a structurally simplified and completely synthetic analogue of macrocyclic ketone halichondrin B. In 2010, eribulin was approved by FDA for the treatment of metastatic breast cancer (MBC). Although several research groups have reported the synthetic efforts toward eribulin, it is still a challenge to prepare eribulin in a large scale due to its complex molecular architecture. Herein, we report a novel and efficient route to the C14–C23 fragment of eribulin from cheap l-arabinose.

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    • 1H and 13C NMR spectra for compounds 916 (PDF)

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