The article illustrated here details the synthesis of lycoposerramine W, a complex natural compound. Researchers at Rice University developed a 10-step method to create this molecule by combining two key fragments: a piperidine and a tetrahydroquinoline. These fragments were prepared using advanced chemical techniques, including biocatalytic oxidation and metal-catalyzed reactions.
The main challenge was joining these fragments. After several failed attempts with conventional methods, the team successfully used a novel "nitrogen deletion" strategy. This involved temporarily adding and then removing a nitrogen atom to facilitate the connection. This innovative approach allowed the researchers to efficiently synthesize lycoposerramine W, showcasing the power of modern synthetic chemistry in creating complex molecules.
For this piece, I focused on the most important step in their synthesis: "Nitrogen Deletion". This cover shows part of the molecule they were working on, with the nitrogen atom in blue strapped to a stick of dynamite, ready to be "deleted".