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Total synthesis of (+)-gelsemine via an organocatalytic Diels–Alder approach

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  • Xiaoming Chen

    (State Key Laboratory of Applied Organic Chemistry, Lanzhou University
    Laboratory of Molecular Engineering, and Laboratory of Natural Product Synthesis, Guangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences)

  • Shengguo Duan

    (State Key Laboratory of Applied Organic Chemistry, Lanzhou University
    Laboratory of Molecular Engineering, and Laboratory of Natural Product Synthesis, Guangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences)

  • Cheng Tao

    (State Key Laboratory of Applied Organic Chemistry, Lanzhou University)

  • Hongbin Zhai

    (State Key Laboratory of Applied Organic Chemistry, Lanzhou University)

  • Fayang G. Qiu

    (Laboratory of Molecular Engineering, and Laboratory of Natural Product Synthesis, Guangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences)

Abstract

The structurally complex alkaloid gelsemine was previously thought to have no significant biological activities, but a recent study has shown that it has potent and specific antinociception in chronic pain. While this molecule has attracted significant interests from the synthetic community, an efficient synthetic strategy is still the goal of many synthetic chemists. Here we report the asymmetric total synthesis of (+)-gelsemine, including a highly diastereoselective and enantioselective organocatalytic Diels–Alder reaction, an efficient intramolecular trans-annular aldol condensation furnishing the prolidine ring and establishing the configuration of the C20 quaternary carbon stereochemical centre. The entire gelsemine skeleton was constructed through a late-stage intramolecular SN2 substitution. The enantiomeric excess of this total synthesis is over 99%, and the overall yield is around 5%.

Suggested Citation

  • Xiaoming Chen & Shengguo Duan & Cheng Tao & Hongbin Zhai & Fayang G. Qiu, 2015. "Total synthesis of (+)-gelsemine via an organocatalytic Diels–Alder approach," Nature Communications, Nature, vol. 6(1), pages 1-7, November.
    • Handle: RePEc:nat:natcom:v:6:y:2015:i:1:d:10.1038_ncomms8204
    DOI: 10.1038/ncomms8204
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