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Asymmetric total synthesis of (−)-lingzhiol via a Rh-catalysed [3+2] cycloaddition

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  • Rong Long

    (Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School
    Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences and Academy for Advanced Interdisciplinary Studies, Peking University)

  • Jun Huang

    (Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School
    Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences and Academy for Advanced Interdisciplinary Studies, Peking University)

  • Wenbin Shao

    (Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School
    Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences and Academy for Advanced Interdisciplinary Studies, Peking University)

  • Song Liu

    (School of Chemistry and Chemical Engineering, Chongqing University)

  • Yu Lan

    (School of Chemistry and Chemical Engineering, Chongqing University)

  • Jianxian Gong

    (Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School
    Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences and Academy for Advanced Interdisciplinary Studies, Peking University)

  • Zhen Yang

    (Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School
    Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences and Academy for Advanced Interdisciplinary Studies, Peking University
    Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China)

Abstract

The development of efficient reactions for the one-pot construction of bicyclic ring systems bearing two quaternary carbon centres at their bridgehead positions represents a significant challenge to synthetic chemistry. The development of new methods capable of overcoming this challenge is highly desirable, because this motif can be found in a wide range of natural products with significant biological activities. Herein, we report an efficient [3+2] cycloaddition reaction between an enal and an alleno rhodium species, which was generated in situ from the corresponding enynol via a retro metal-propargylation reaction, to give [3.3.0] and [3.4.0] bicyclic systems bearing two quaternary atoms at their bridgehead positions. The developed chemistry has been successfully applied to the asymmetric total synthesis of natural product (−)-lingzhiol (4) for the first time in 17 steps.

Suggested Citation

  • Rong Long & Jun Huang & Wenbin Shao & Song Liu & Yu Lan & Jianxian Gong & Zhen Yang, 2014. "Asymmetric total synthesis of (−)-lingzhiol via a Rh-catalysed [3+2] cycloaddition," Nature Communications, Nature, vol. 5(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:5:y:2014:i:1:d:10.1038_ncomms6707
    DOI: 10.1038/ncomms6707
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