UC San Diego

The work presented herein is the conclusion of synthetic studies toward the total synthesis of norzoanthamine. This dissertation on the norzoanthamine synthetic studies will be divided into 3 sections: (1) an introduction describing the norzoanthamine family along with their biological significance and previous studies; (2) a stereoselective synthesis of the ABC ring system, and the crucial development of the fully functionalized C ring; (3) a biomimetic approach towards norzoanthamine; which will discuss studies to create the C ring from a polyene system through a Diels-Alder reaction, studies to synthesize the A ring through a sigmatropic rearrangement, studies to generate the BC ring through an intramolecular Diels-Alder reaction from carvone as a chiral pool, development of isocarvone, and studies of 2-acylamino 1,3 dienes as a viable synthon to form the BC ring through a [4+2] cycloaddition reaction