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Divergent and Efficient Syntheses of the Lycopodium Alkaloids (−)-Lycojaponicumin C, (−)-8-Deoxyserratinine, (+)-Fawcettimine, and (+)-Fawcettidine

Authors

  • Si-Hua Hou,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China)
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  • Prof. Dr. Yong-Qiang Tu,

    Corresponding author
    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China)
    • State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China)

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  • Lin Liu,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China)
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  • Prof. Dr. Fu-Min Zhang,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China)
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  • Prof. Dr. Shao-Hua Wang,

    Corresponding author
    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China)
    2. School of Pharmacy, Lanzhou University, Lanzhou 730000 (P. R. China)
    • State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China)

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  • Dr. Xiao-Ming Zhang

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P. R. China)
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  • This work was supported by the NSFC (21072085, 21102061, 21202073, 21290180, and 21272097), the “973” Program of MOST (2010CB833203), the “111” Program of MOE, and the Major Project of MOST (2012ZX 09201101-003). We thank Prof. Shi-Shan Yu of the Institute of Materia Medica Chinese Academy of Medical Sciences and Peking Union Medical College for providing a sample of 1.

Abstract

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Four from one: The four title alkaloids (structures shown in blue box) have been synthesized by using a common versatile intermediate with a 6/5/5 tricyclic skeleton. This tricyclic intermediate could be easily assembled by using an intramolecular carbene addition/cyclization and a Dieckmann condensation/Tsuji–Trost allylation as key steps.

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