A transannular Cope approach toward the core structure of isocyclocitrinol

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.