As an especially unique target for chemical synthesis, diazonamide A has the potential to be constructed through a plethora of synthetic routes, each attended by different challenges and opportunities for discovery. In this article, we detail our second total synthesis of diazonamide A through a sequence entirely distinct from that employed in our first campaign, one whose success required the development of several special strategies and tactics. We also disclose our complete studies regarding the chemical biology of diazonamide A and its structural congeners, and more fully delineate the scope of our protocol for Robinson-Gabriel cyclodehydration using pyridine-buffered POCl(3).

Here we report a total synthesis of the pharmacologically significant morphinan alkaloid, oxycodone.

A rationally designed, serial point-to-axial and axial-to-point stereoinduction and its integration into a multi-step and target-oriented organic synthesis was demonstrated in a novel chemical method to access morphinans and it is potentially applicable to other structurally related alkaloids.

Synthesis of the strained cyclophane alkaloid haouamine A has been accomplished via a late-stage and strain-accelerated oxidation to access the challenging biphenol cyclophane system.