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    Asymmetric Total Synthesis of Pre-schisanartanin C
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    • Yan-Long Jiang
      Yan-Long Jiang
      Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, China
      More by Yan-Long Jiang
      Orcidhttp://orcid.org/0000-0002-6535-4198
    • Hai-Xin Yu
      Hai-Xin Yu
      Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, China
      More by Hai-Xin Yu
      Orcidhttp://orcid.org/0000-0002-2815-1789
    • Yong Li
      Yong Li
      Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, China
      More by Yong Li
      Orcidhttp://orcid.org/0000-0003-1463-6854
    • Pei Qu
      Pei Qu
      Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, China
      More by Pei Qu
      Orcidhttp://orcid.org/0000-0002-7454-3636
    • Yi-Xin Han
      Yi-Xin Han
      Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, China
      More by Yi-Xin Han
      Orcidhttp://orcid.org/0000-0002-4941-092X
    • Jia-Hua Chen*
      Jia-Hua Chen
      Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, China
      *[email protected]
      More by Jia-Hua Chen
      Orcidhttp://orcid.org/0000-0002-6405-816X
    • Zhen Yang*
      Zhen Yang
      Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, China
      State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China
      Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, China
      *[email protected]
      More by Zhen Yang
      Orcidhttp://orcid.org/0000-0001-8036-934X
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2020, 142, 1, 573–580
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    https://doi.org/10.1021/jacs.9b11872
    Published December 2, 2019
    Copyright © 2019 American Chemical Society
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    Abstract

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    Pre-schisanartanin C belongs to the family of Schisandra nortriterpenoids with potent antihepatitis, antitumor, and anti-HIV activities. This paper presents the enantioselective total synthesis of pre-schisanartanin C (1). An important step in the total synthesis of 1 is gold-catalyzed intramolecular cyclopropanation of a 1,8-enyne substrate bearing a secondary ester group at the propargylic position to prepare a bicyclo[6.1.0]nonane core. Additional highlights include (i) an asymmetric Diels–Alder reaction to install the initial C5 stereogenic center of 1 and (ii) a sequential Pd-catalyzed Stille coupling, regio- and stereoselective Sharpless asymmetric dihydroxylation, and a subsequent intramolecular lactonization to construct the side chain of 1. The developed chemistry paves the way for the total syntheses of other family members bearing highly rigid bicyclo[6.1.0]nonane cores.

    Copyright © 2019 American Chemical Society

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    Cited By

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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2020, 142, 1, 573–580
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.9b11872
    Published December 2, 2019
    Copyright © 2019 American Chemical Society
    Request reuse permissions

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