UC San Diego

The work described herein is a culmination of synthetic studies in the area of cembrenolide natural products, compounds that are synthetically intriguing not only for their highly intricate structures, but also for their array of bioactivities. The synthetic studies toward this family of natural products is divided into 4 chapters : (1) an overview of the first generation of the synthesis with discussion of the total synthesis of norcem- brenolide B and scabrolide D; (2) a discussion of the second generation of the synthe- sis of the family of cembrenolides, specifically, the introduction of the C13 hydroxy functionality and its oxidative rearrangement patterns; (3) an overview of the third gen- eration which involves further carbon skeletal rearrangements toward the synthesis of highly complex cembrenolides such as verrillin; (4) concluding remarks which describe the evolution of each generation and highlight each generation's strengths. Discussions of synthetic strategies and design are also discussed in great detail