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Progress in Chemistry 2018, Vol. 30 Issue (5): 578-585 DOI: 10.7536/PC171131 Previous Articles   Next Articles

• Review •

Total Synthesis of the Akuammiline Alkaloid Strictamine

Xiaoyu Liu1, Tao Xiao2, Yong Qin1*   

  1. 1. West China School of Pharmacy, Sichuan University, Chengdu 610041, China;
    2. School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, China
  • Received: Revised: Online: Published:
  • Supported by:
    The work was supported by the National Natural Science Foundation of China (No. 21732005).
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Due to their complex and diverse structures and significant bioactivities, the chemical synthesis of the akuammiline alkaloids has been highly pursued in the chemical community. Strictamine, as one of the representative members in this natural product family, is structurally featured by a cage like methanoquinolizidine framework and an all-carbon quaternary stereogenic center at C7, posing a great challenge in synthesis. Pursuit in the total synthesis of strictamine has a history of over four decades; however, the breakthroughs came until the recent two years. This review briefly summarizes the three total syntheses and four formal syntheses of strictamine that have been reported since 2016, by highlighting the key strategies and reactions employed in each of the synthesis. Moreover, perspectives in this research field have also been suggested at the end of this review.
Contents
1 Introduction
2 Total synthesis and formal total synthesis of strictamine
2.1 Asymmetric total synthesis of (+)-strictamine by the Garg group
2.2 Total synthesis of (±)-strictamine by the Zhu group
2.3 Total synthesis of (±)-strictamine by the Zu group
2.4 Formal synthesis of (±)-strictamine by the Fujii/Ohno group
2.5 Formal synthesis of (+)-strictamine by the Snyder group
2.6 Formal synthesis of (±)-strictamine by the Gaich group
2.7 Formal synthesis of (+)-strictamine by the Qin group
3 Conclusion and outlook
Key words: akuammiline alkaloid, strictamine, natural product, total synthesis

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