灯台生物碱具有复杂多样的结构和显著的生理活性，针对此类分子的化学合成引起了有机化学界的广泛关注。其中的代表性化合物strictamine在结构上具有笼状的methanoquinolizidine核心骨架和C7位全碳季碳手性中心，在合成上具有重要挑战。关于该化合物的全合成已有超过40年的研究历史，而直到最近两年才取得突破性的进展。本文针对2016年以来关于strictamine的三条全合成和四条形式合成路线进行简要介绍，主要剖析了各条合成路线中的关键策略和反应，并对进一步的研究进行了展望。
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
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