This dissertation focuses on the development of novel chemical reactions for enhancing the efficiency of synthesis. In particular, we disclose the development of a tandem
fragmentation-olefination reaction for the synthesis of 1,6-enynes and its applications to the syntheses of several natural products. The first chapter reviews fragmentation methodologies
for the preparation of alkynes, with insights and discussion in historical aspects, mechanisms, stereoelectronics, and tactics. The second chapter starts with a brief background on values
of 1,6-enynes leading to various cyclic and polycyclic structures, currently available methods for the preparation of 1,6-enynes, and challenges these methods are facing, especially in
preparing neopentyl tethered 1,6-enynes. Then we describe our development of the tandem fragmentation-olefination reaction, which took advantage of tandem process to overcome intermediate
instability, providing the final products more efficiently. In chapter 3, this method was applied in the syntheses of several natural products, either to showcase the efficiency of the
methodology or to supply material with potential bioactivities. In case of alcyopterosin A, the synthesis was shortened by half when compared with previous approaches. We also have
established a divergent approach to both illudalic acid and illudinine. The approach relies on two key transformations: a tandem fragmentation-Knoevenagel condensation and an inversed
electron demand intramolecular dehydrogenative Diels-Alder reaction. / A Dissertation submitted to the Department of Chemistry and Biochemistry in partial fulfillment of the requirements for the degree of Doctor of
Philosophy. / Fall Semester 2015. / November 11, 2015. / fragmentation reaction, natural products, sesquiterpene, tandem/cascade/domino reaction, total synthesis / Includes bibliographical references. / Gregory B. Dudley, Professor Directing Dissertation; Don Levitan, University Representative; Igor Alabugin, Committee Member; Brian Miller, Committee
Member.
| Identifer | oai:union.ndltd.org:fsu.edu/oai:fsu.digital.flvc.org:fsu_291299 |
| Contributors | Hoang, Tung T. (Tung Thanh) (authoraut), Dudley, Gregory B. (professor directing dissertation), Levitan, Don R. (university representative), Alabugin, Igor V. (committee member), Miller, Brian G. (committee member), Florida State University (degree granting institution), College of Arts and Sciences (degree granting college), Department of Chemistry and Biochemistry (degree granting department) |
| Publisher | Florida State University |
| Source Sets | Florida State University |
| Language | English, English |
| Detected Language | English |
| Type | Text, text |
| Format | 1 online resource (146 pages), computer, application/pdf |
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