The isolation of flueggenines A and B by Yue and co-workers in 2006 has triggered a burst of isolation reports of dimeric and oligomeric securinega alkaloid natural products. The compelling molecular structures of these compounds with various modes of connection between monomeric securinega units have posed intriguing challenges to the synthetic organic community. Herein, we have categorized high-order securinega alkaloids based on their biosynthetic mode of dimerization or oligomerization. We then have compiled all reported syntheses of dimeric securinega alkaloids based on our classification.