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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 1: 313 - 319

DOI: https://doi.org/10.6023/cjoc202206034

Asymmetric Synthesis of (–)-Colchicine and Its Natural Analog (–)-N-Acetylcolchicine Methyl Ether

  • Liu-Yang Pu ,
  • Zhiyue Li ,
  • Limin Li ,
  • Yucui Ma ,
  • Min Ma ,
  • Shengquan Hu ,
  • Zhengzhi Wu
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  • a Integrated Chinese and Western Medicine Postdoctoral Research Station, Jinan University, Guangzhou 510632
    b Shenzhen Institute of Translational Medicine, Shenzhen Second People’s Hospital, The First Affiliated Hospital of Shenzhen University, Shenzhen, Guangdong 518035
    c Shenzhen Institute of Geriatrics, Shenzhen, Guangdong 518035
† These authors contributed equally to this work.
* Corresponding authors. E-mail: ;
;

Received date: 2022-06-20

  Revised date: 2022-07-26

  Online published: 2022-09-02

Supported by

Shenzhen Science and Technology Innovation Commission(JSGG20210901145539016); Shenzhen Science and Technology Innovation Commission(JCYJ20190812171005713); Shenzhen Science and Technology Innovation Commission(JCYJ20210324121611032); Shenzhen Baoan Chinese Medicine Development Foundation(2020KJCX-KTYJ-215); Shenzhen Excellent Scientific and Technological Innovation Talents Training Project-PhD Initiation Program(RCBS20210706092212002); Guangdong Basic and Applied Basic Research Foundation(2020A1515011427); Guangdong Basic and Applied Basic Research Foundation(2022A1515011777)

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Abstract

(–)-Colchicine and its natural analogue (–)-N-acetylcolchinol methyl ether have been synthesized in a com- paratively conciser asymmetric synthetic approach. Firstly, the carbon framework was constructed by Aldol condensation of simple aldehydes and ketones, and then the chiral amine intermediates were synthesized economically and efficiently through asymmetric reductive amination with chiral tert-butanesulfinamide. The 3-rings skeleton of colchicine and related alkaloids was then constructed by oxidation with hypervalent iodine reagent. Our strategy provides an efficient method for the convenient and economical synthesis of these alkaloids.

Key words： colchicine; (–)-N-acetylcolchinol methyl ether; tert-butanesulfinamide; asymmetric synthesis

Cite this article

Liu-Yang Pu , Zhiyue Li , Limin Li , Yucui Ma , Min Ma , Shengquan Hu , Zhengzhi Wu . Asymmetric Synthesis of (–)-Colchicine and Its Natural Analog (–)-N-Acetylcolchicine Methyl Ether[J]. Chinese Journal of Organic Chemistry, 2023 , 43(1) : 313 -319 . DOI: 10.6023/cjoc202206034

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