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Gold-Catalyzed Cycloadditions: An Approach Toward Complex Molecular Frameworks via Transannular, Intermolecular, and Intramolecular Methods

Bailey, Lauren N.
http://rave.ohiolink.edu/etdc/view?acc_num=miami1272550184

Abstract Details

2010, Master of Science, Miami University, Chemistry and Biochemistry.
Many biologically active compounds contain multiple fused rings, and often the synthesis of these compounds can be quite complex. Efforts to produce these intricate molecular frameworks through cycloaddition reactions are advantageous, with the ability to produce fused ring structures in only one step. This thesis describes the work towards the synthesis of fused ring products through gold-catalyzed cycloadditions. The construction of various carbocycles was achieved through transannular, intermolecular, and intramolecular methods. Rapid assembly of the core structure of Cortistatin A, a potent antiangiogenesis natural product, was achieved through a transannular [4 + 3] cycloaddition from a macrocyclic precursor. Additionally, the [4 + 3] cycloaddition reaction was extended to the intermolecular variant using propargyl ester and diene precursors. Progress towards the application of intramolecular gold-catalyzed cycloadditions is also described. Where appropriate, investigation of the regioselectivity and stereochemistry of these reactions is analyzed, and mechanistic pathways are also discussed.
Benjamin W. Gung (Advisor)
Richard T. Taylor (Committee Chair)
C. Scott Hartley (Committee Member)
Shouzhong Zou (Committee Member)
248 p.
Organic Chemistry
gold catalysis; [4 + 3] cycloadditions; transannular; cyclopropanation

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Citations

  • Bailey, L. N. (2010). Gold-Catalyzed Cycloadditions: An Approach Toward Complex Molecular Frameworks via Transannular, Intermolecular, and Intramolecular Methods [Master's thesis, Miami University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=miami1272550184

    APA Style (7th edition)

  • Bailey, Lauren. Gold-Catalyzed Cycloadditions: An Approach Toward Complex Molecular Frameworks via Transannular, Intermolecular, and Intramolecular Methods. 2010. Miami University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=miami1272550184.

    MLA Style (8th edition)

  • Bailey, Lauren. "Gold-Catalyzed Cycloadditions: An Approach Toward Complex Molecular Frameworks via Transannular, Intermolecular, and Intramolecular Methods." Master's thesis, Miami University, 2010. http://rave.ohiolink.edu/etdc/view?acc_num=miami1272550184

    Chicago Manual of Style (17th edition)

miami1272550184
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© 2010, all rights reserved.
This open access ETD is published by Miami University and OhioLINK.