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Synthesis of Huacat® Analogues As Novel Organocatalysts for the Formation of Asymmetric C-C Bonds Kenneth Laboy

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Synthesis of Huacat® Analogues As Novel Organocatalysts for the Formation of Asymmetric C-C Bonds Kenneth Laboy Loma Linda University TheScholarsRepository@LLU: Digital Archive of Research, Scholarship & Creative Works Loma Linda University Electronic Theses, Dissertations & Projects 9-2016 Synthesis of HuaCat® Analogues as Novel Organocatalysts for the Formation of Asymmetric C-C Bonds Kenneth Laboy Follow this and additional works at: http://scholarsrepository.llu.edu/etd Part of the Biochemistry, Biophysics, and Structural Biology Commons, and the Medicinal and Pharmaceutical Chemistry Commons Recommended Citation Laboy, Kenneth, "Synthesis of HuaCat® Analogues as Novel Organocatalysts for the Formation of Asymmetric C-C Bonds" (2016). Loma Linda University Electronic Theses, Dissertations & Projects. 382. http://scholarsrepository.llu.edu/etd/382 This Thesis is brought to you for free and open access by TheScholarsRepository@LLU: Digital Archive of Research, Scholarship & Creative Works. It has been accepted for inclusion in Loma Linda University Electronic Theses, Dissertations & Projects by an authorized administrator of TheScholarsRepository@LLU: Digital Archive of Research, Scholarship & Creative Works. For more information, please contact [email protected]. LOMA LINDA UNIVERSITY School of Medicine in conjunction with the Faculty of Graduate Studies ____________________ Synthesis of HuaCat® Analogues as Novel Organocatalysts for the Formation of Asymmetric C-C Bonds by Kenneth Laboy ____________________ A Dissertation submitted in partial satisfaction of the requirements for the degree Master of Science in Biochemistry ____________________ September 2016 © 2016 Kenneth Laboy All Rights Reserved Each person whose signature appears below certifies that this thesis in his opinion is adequate, in scope and quality, as a thesis for the degree Master of Science. , Chairperson David Weldon, Associate Professor of Pharmaceutical and Administrative Sciences Willie Davis, Associate Professor of Pharmaceutical and Administrative Sciences Nathan Wall, Associate Professor of Biochemistry and Molecular Biology iii ACKNOWLEDGEMENTS I would like to express my deepest gratitude to my advisor Dr. David Weldon for giving me the opportunity to embark on this long journey with him in the field of Medicinal Chemistry. It’s been a long road and I know it’s been tough for him trying to teach me to keep my head down and screwed on straight. Throughout it all he had my back and became my family. Doc, I want to thank you for everything, and hope that you can be proud of the work you put in and sacrifices you made to make me a better man. I would also like to give thanks to Dr. Marvin Payne for introducing me into the field of science in a manner that gave me a thirst for knowledge that I never had before. I feel indebted to him for all the advice and direction you’ve given me over the years. I still remember when you brought me into your office and told me to go to the VA for help. All the times you gave me a ride to therapy and watched out for me really made a difference in my life. I’d also like to thank Dr. Nathan Wall for being my swim buddy, keeping me motivated when I wanted to quit. Moreover, I feel so grateful to him for kicking me in the rear when I needed it and patting me on the back when it was necessary. Thanks for being patient with me sir. To Dr. Willie Davis, thank you for your support and guidance throughout these years in the lab. Skipper, you’ve always kept from becoming complacent and your leadership was key to keeping me accountable for my actions. And finally, I would like to thank the School of Pharmacy and Dr. Rashid Mosavin for providing me the opportunity to study and pursuit my goals. iv CONTENT Approval Page .................................................................................................................... iii Acknowledgements ............................................................................................................ iv List of Figures .................................................................................................................. viii List of Tables .......................................................................................................................x List of Abbreviations ......................................................................................................... xi Abstract ............................................................................................................................ xiii Chapter 1. Introduction ..............................................................................................................1 The importance/significance of carbon-carbon bond formation ........................1 The significance of a broad selection of catalysts and reagents ........................8 Various methods of carbon-carbon bond formation ........................................13 Stereochemistry and Regiochemistry ..............................................................20 The major advantages of HuaCat® ..................................................................28 2. Materials and Methods ...........................................................................................36 General ................................................................................................................. 3. Synthetic strategy, Results, and Discussion ...........................................................39 Design Strategy ................................................................................................39 Examination of Results and Discussion ...........................................................45 Conclusion .......................................................................................................48 Experimental section ........................................................................................49 Various attempted experimental procedures ..............................................54 References ..........................................................................................................................67 Appendices A. Flash chromatography purification reports .........................................................87 B. NMR Analysis reports ......................................................................................139 v Carbon NMR .....................................................................................................139 Proton NMR ......................................................................................................153 C. Vita ....................................................................................................................194 vi FIGURES Figures Page 1. Aldol condensation reaction ....................................................................................4 2. Citrate synthase aldol condensation reaction of the first step of the Krebs cycle .........................................................................................................................4 3. Aldolase catalyzed reaction of GAP & DHAP ........................................................5 4. Biosynthesis of Lanosterol .......................................................................................6 5. Metal catalyst framework for C-C bonds .................................................................7 6. Ziegler-Natta catalysis of isoprene units ..................................................................8 7. Catalyzed carboxylation of methane ........................................................................9 8. Palladium catalyzed synthesis of Lactones ............................................................10 9. Ruthenium catalyzed synthesis of Vinyl-carbamates ............................................10 10. Michael addition reaction ......................................................................................15 11. Mannich reaction ...................................................................................................16 12. Diels-Alder reaction ...............................................................................................17 13. Horner-Wadsworth-Emmons (HWE) reaction ......................................................18 14. Suzuki reaction scheme and catalytic cycle with Pd .............................................20 15. Example of stereoisomers using 2-bromo-3-chlorobutane ....................................21 16. Structures of Carvone ............................................................................................22 17. Structure of Ibuprofen ............................................................................................23 18. Structure of Thalidamide .......................................................................................24 19. Markovnikov addition ............................................................................................26 20. Zimmer model for chair confirmation transition state ...........................................30 21. Proposed mechanism for Proline aldol reaction with transition state chair confirmation ...........................................................................................................31 vii 22. Tetrazoles (A); Sulfonamides (B) ..........................................................................33 23. HuaCat® facilitated asymmetric reactions: (A) Aldol reaction (B) Mannich reaction (C) intramolecular Michael addition .........................................35 24. Desired products ....................................................................................................36
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