Citation/Abstract

This thesis describes the efforts of Professor James Leighton and myself toward the construction of the core structure of isocyclocitrinol. Our first two approaches toward the 10-membered ring system using ring closing metathesis are discussed. The next chapter discusses the new approaches toward the synthesis of the cyclopentane piece cumulating in the successful epoxy-silane approach. The next three chapters discuss the macrocyclic Suzuki, ketene-aldeyde [2+2], and Ramberg-Bäcklund strategy. Finally, our efforts in performing a ring-contracting Ireland-Claisen reaction for the construction of the 10-membered ring are discussed.