Biomimetic total synthesis of ten Securinega alkaloids

Abstract

The Securinega alkaloids are a diverse family of polycyclic alkaloids with broad biological importance. In this study, a formal [4 + 2] cycloaddition strategy has been used to complete the biomimetic total synthesis of six Securinega alkaloids, notably using biosynthetically plausible scaffold-forming steps and aqueous reaction conditions. A further four alkaloids were also generated via subsequent rearrangement reactions. Altogether, the total syntheses of ten Securinega alkaloids are described, in one or two linear steps from proposed biosynthetic precursor menisdaurilide. These results support the hypothesis that the same or similar pathways may operate in planta.