Total synthesis of (-)-securingine G

Abstract

In this study, we present the first total synthesis of (-)-securingine G. Diverging from the proposed biosynthetic pathway, our approach involves the addition of nucleophilic pyridine anion species to the electrophilic menisdaurilide congener. Crucially, incorporating a weakly basic yet nucleophilic tri(2-pyridinyl)lanthanum complex proved essential to circumvent undesired base-mediated pathways during the key coupling reaction. Notably, we introduce n-Bu3La<middle dot>5LiCl as a new exchange reagent, facilitating efficient halide/lanthanum exchange of (hetero)aryl halides. In this study, we present the first total synthesis of (-)-securingine G.