Progress towards the total synthesis of debromophycolide

Abstract

The structure of debromophycolide provides a novel synthetic target that could provide synthetic insight into several other members of the bromophycolide family. Our synthetic efforts toward the total synthesis of debromophycolide are described. The discussion begins with the description of a planned convergent approach to the total synthesis of debromophycolide. Key disconnections dissect the molecule into four distinct fragments that can be joined in multiple ways to incorporate flexibility to the synthesis. Our approach begins with the construction of a benzyl-cyclopentenyl fragment utilizing a transition metal cross-coupling reaction. Then focus shifts towards a functionalized aliphatic fragment, which incorporates a conjugate addition reaction to link the two fragments. Efforts to implement this plan are then described.