Iboga alkaloids are a large family in natural products that possess both indole and isoquinuclidine moieties. Besides the structural features, their potential biological activities including anti-addiction, anti-cancer, and anti-bacterial have attracted enormous attentions and led to development of innovative synthetic routes to this family of natural products.
One of nature’s evolution strategy is maximizing the secondary metabolites from a common precursor. Inspired by this biosynthetic strategy, our group showed that some alkaloids (which we coined the term “post-iboga” alkaloids) were presumably biosynthetically derived from iboga alkaloids.1 In our previous studies, we were able to access type II post-iboga alkaloids voatinggine, tabertinggine as well as type III post-iboga alkaloid dippinine B.2 Herein, we present the broadened scope of synthetically accessible type III post-iboga alkaloids. We depict the biogenetically inspired transformation of catharanthine to type III post iboga alkaloids such as dippinine C and tronocarpine.
1. Lim, H.; Seong, S.; Han, S. Synthesis 2019, 51, 2737.
2. Seong, S.; Lim, H.; Han, S. Chem 2019, 5, 353.