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Applications of Alkynogenic Fragmentation Products Derived from Vinylogous Acyl Triflates

Title: Applications of Alkynogenic Fragmentation Products Derived from Vinylogous Acyl Triflates.
Name(s): Ramsubhag, Ron Robert, author
Fajer, Piotr G., university representative
Saltiel, Jack, committee member
Zhu, Lei, 1978-, committee member
Florida State University, degree granting institution
College of Arts and Sciences, degree granting college
Department of Chemical and Biomedical Engineering, degree granting department
Type of Resource: text
Genre: Text
Doctoral Thesis
Issuance: monographic
Date Issued: 2017
Publisher: Florida State University
Place of Publication: Tallahassee, Florida
Physical Form: computer
online resource
Extent: 1 online resource (101 pages)
Language(s): English
Abstract/Description: Carbon-carbon bond formation is the foundation to synthesizing complex molecules and has gathered the attention of many synthetic chemists. One must keep in mind that these reactions are dependent on materials for a specific agenda when tackling a structural framework, which may require additional steps to create, and at times, are difficult to prepare. As significant as C-C bond formation reactions are, these minor setbacks may draw caution when synthesizing a complicated molecule whose structural framework cannot be easily accessed by the unity of two fragments. On the other hand, the less familiar C-C bond cleavage reactions have, over time, demonstrated the potential to generate unique structural building blocks that can be used to overcome certain obstacles that other synthetic methods cannot provide. Here, we will be focusing on concerted anionic five-center fragmentation reactions using vinylogous acyl triflates. The generated alkynogenic fragments will then be used in different applications. We will begin by looking at chemoselective “click” reactions. The strained-promoted alkyne is synthesized by a tandem intramolecular nucleophilic addition / fragmentation. The expanded ring will contain a strained cycloalkyne which will later be tethered to a terminal alkyne. The diyne will be used to provide an example of a “dual-click” coupling via SPAAC or CuAAC in either sequential order. Next, we will expand the tandem fragmentation / olefination methodology developed in this work to include dienynes. The dienyne provides the structural backbone needed to produce neopentylene indanes. This methodology is used to design new ibuprofen derivatives that demonstrate rigidity and increase hydrophobicity to modulate the molecular pharmacology of ibuprofen.
Identifier: FSU_FALL2017_Ramsubhag_fsu_0071E_14133 (IID)
Submitted Note: A Dissertation submitted to the Department of Chemistry and Biochemistry in partial fulfillment of the requirements for the degree of Doctor of Philosophy.
Degree Awarded: Fall Semester 2017.
Date of Defense: August 24, 2017.
Bibliography Note: Includes bibliographical references.
Advisory Committee: Piotr Fajer, University Representative; Jack Saltiel, Committee Member; Lei Zhu, Committee Member.
Subject(s): Chemistry, Organic
Persistent Link to This Record:
Owner Institution: FSU

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Ramsubhag, R. R. (2017). Applications of Alkynogenic Fragmentation Products Derived from Vinylogous Acyl Triflates. Retrieved from