Strategies and Tactics for the Synthesis of Complex Alkaloids

Efforts to achieve the laboratory synthesis of complex natural products have long served as a means to advance the science of organic chemistry. Indeed, core physical organic principles, new reagents and synthetic transformations, effective strategies for stereocontrolled synthesis, and useful pharmaceutical agents are but a few advances that have issued from such endeavors over the course of the past century. Within this review are recounted selected research programs from the author's laboratory seeking to add to that repertoire of discoveries by targeting complex polycyclic alkaloids for synthesis. Advances resulting from these studies include new strategies for the rapid synthesis of intricate molecular domains, reaction processes and sequences capable of accessing a range of diversity across several alkaloid classes, examples of achieving family-level synthetic solutions from common synthetic building blocks, and a unique perspective on effecting the laboratory synthesis of dimeric materials when direct mergers fail.