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.
|Advisor:||Leighton, James L.|
|School Location:||United States -- New York|
|Source:||DAI-B 69/10, Dissertation Abstracts International|
|Keywords:||Ireland-Claisen reaction, Isocyclocitrinol, Macrolactones, Ring-closing metathesis, Transannular Cope|
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