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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. |
| Commitee: | |
| School: | Columbia University |
| School Location: | United States -- New York |
| Source: | DAI-B 69/10, Dissertation Abstracts International |
| Source Type: | DISSERTATION |
| Subjects: | Organic chemistry |
| Keywords: | Ireland-Claisen reaction, Isocyclocitrinol, Macrolactones, Ring-closing metathesis, Transannular Cope |
| Publication Number: | 3333478 |
| ISBN: | 978-0-549-85600-9 |
