State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China

Oxidative coupling occupies a special position among organic reactions owing to its ability to directly construct carbon-carbon and carbon-heteroatom bonds between two nucleophiles in a single step without prefunctionalization. Oxidative coupling is one of nature’s most commonly used synthetic tools and many plants utilize metalloenzyme-catalyzed single-electron oxidative coupling reactions for the production of specific metabolites that are essential for plant growth and protection. Serotobenine, decursivine, flavumindole, and montamine possess very similar structural features which are related with moschamine. The biosynthetic pathways of these alkaloids might involve an oxidative cross- or homo-coupling. We found that both of the cross- and homo-coupling could be occurred and controlled under specific reaction conditions. Using this biomimetic reaction, serotobenine and decursivine were high efficiently total synthesized. The dimer montamine was also prepared and its structural was reassigned by comparison of the spectra of isolated and synthetic compounds.