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Ester Resveratrol Analogues, Chromium Trioxide Oxidation of Terpenes, and Synthesis of Mimics of (-)-Englerin A

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Ester Resveratrol Analogues, Chromium Trioxide Oxidation of Terpenes, and Synthesis of Mimics of (-)-Englerin A Brigham Young University BYU ScholarsArchive Theses and Dissertations 2014-08-01 Synthesis of 4'-Ester Resveratrol Analogues, Chromium Trioxide Oxidation of Terpenes, and Synthesis of Mimics of (-)-Englerin A Mark Jeffrey Acerson Brigham Young University - Provo Follow this and additional works at: https://scholarsarchive.byu.edu/etd Part of the Biochemistry Commons, and the Chemistry Commons BYU ScholarsArchive Citation Acerson, Mark Jeffrey, "Synthesis of 4'-Ester Resveratrol Analogues, Chromium Trioxide Oxidation of Terpenes, and Synthesis of Mimics of (-)-Englerin A" (2014). Theses and Dissertations. 5458. https://scholarsarchive.byu.edu/etd/5458 This Dissertation is brought to you for free and open access by BYU ScholarsArchive. It has been accepted for inclusion in Theses and Dissertations by an authorized administrator of BYU ScholarsArchive. For more information, please contact [email protected], [email protected]. Synthesis of 4’-Ester Resveratrol Analogues, Chromium Trioxide Oxidation of Terpenes, and Synthesis of Mimics of (–)-Englerin A Mark Jeffrey Acerson A dissertation submitted to the faculty of Brigham Young University in partial fulfillment of the requirements for the degree of Doctor of Philosophy Merritt B. Andrus, Chair Steven L. Castle Matt A. Peterson Joshua L. Price Richard K. Watt Department of Chemistry and Biochemistry Brigham Young University August 2014 Copyright © 2014 Mark Jeffrey Acerson All Rights Reserved ABSTRACT Synthesis of 4’-Ester Resveratrol Analogues, Chromium Trioxide Oxidation of Terpenes, and Synthesis of Mimics of (–)-Englerin A Mark Jeffrey Acerson Department of Chemistry and Biochemistry, BYU Doctor of Philosophy 4’-ester analogues of resveratrol were synthesized using reaction conditions developed to produce mono-ester products in the presence of two other unprotected phenols. Basic conditions were employed to deprotonate the most acidic 4’ phenol followed by addition of anhydrides or acid chlorides to give the ester product. The reaction favored 4’-ester formation in polar aprotic solvents with DMSO being the optimal solvent. (–)-Englerin A is a guaiane-type sesquiterpene containing two ester side chains. Mimics of (–)-englerin A were proposed that retained the ester side chains while replacing the non-polar core with less complicated structures. These proposed mimic cores would maintain the three- dimensional positioning of the esters which are responsible for the anti-cancer activity of (–)- englerin A. Three mimics were synthesized using the bicyclic terpenes borneol and fenchol. Installation of the second ester on the terpene core was accomplished throught the development and optimization of a unique methylene oxidation using chromium trioxide in glacial acetic acid. These mimics were screened against two kidney cancer cell lines. The compounds were shown to have IC50 (inhibitory concentration for 50 % of cells) values above 30 μM. Keywords: resveratrol, englerin A, analogue, mimic, polyphenol, anti-viral, anti-cancer, methylene oxidation, selective esterification ACKNOWLEDGEMENTS I would like to thank Dr. Merritt Andrus for teaching me organic chemistry in the classroom and then giving me the opportunity to apply my knowledge in the lab. I also thank him for his great ideas and advice in helping me solve many problems I encountered while trying to get reactions to work. I thank my committee members Steven Castle, Matt Peterson, Paul Savage, and Richard Watt both for the time spent teaching me in the classroom and mentoring given. I owe so much to my wife and family for their support during the time I spent obtaining my doctorate degree. Aersta always gave me support if I had to stay late at the lab to finish up a column or reaction. I thank Brigham Young University for the opportunity to work in such a wonderful building as the Benson and for the financial support provided during the years of my education. I also thank the Cancer Research Center at Brigham Young University for allowing me to pursue cancer research for two summers during my doctorate degree. Table of Contents 1. Synthesis of 4’-Ester Resveratrol Analogues and Evaluation of Anti-cancer Activity ........... 1 1.1 Introduction ...................................................................................................................... 1 1.1.1 Discovery .................................................................................................................. 1 1.1.2 Biological Activity .................................................................................................... 2 1.1.3 Total Synthesis of Resveratrol and Analogues ......................................................... 3 1.1.4 Mono-esterification of Polyphenols .......................................................................... 5 1.2 Results and Discussion ..................................................................................................... 7 1.2.1 Synthesis of Mono-Ester Analogues of Resveratrol ................................................. 7 1.2.2 Assessing Anti-cancer Activity of Resveratrol Analogues ..................................... 13 1.3 Conclusion and Future Work ......................................................................................... 14 2. Selective Oxidation using Chromium Trioxide ..................................................................... 16 2.1 Introduction .................................................................................................................... 16 2.2 Results and Discussion ................................................................................................... 21 2.2.1 Oxidation Conditions .............................................................................................. 21 2.2.2 CrO3 Oxidation Mechanism .................................................................................... 28 2.3 Conclusion and Future Work ......................................................................................... 30 3. (–)-Englerin A Mimic Synthesis and Anti-cancer Evaluation ............................................... 32 3.1 Introduction .................................................................................................................... 32 3.1.1 Discovery ................................................................................................................ 32 3.1.2 Biological Activity .................................................................................................. 33 3.1.3 Total Synthesis of Englerin A ................................................................................. 33 3.1.4 Mimics of Natural Products .................................................................................... 35 iv 3.1.5 Englerin A Mimic Design ....................................................................................... 37 3.2 Results and Discussion ................................................................................................... 40 3.2.1 Assessing Anti-cancer Activity of Englerin A Mimics .......................................... 44 3.3 Conclusions and Future Work ........................................................................................ 46 4. Experimental Details and Data .............................................................................................. 47 4.1 General Method and Materials ....................................................................................... 47 4.2 Synthesis of Resveratrol Analogues ............................................................................... 47 4.3 Oxidation Optimization .................................................................................................. 59 4.4 Synthesis of Englerin A Mimics .................................................................................... 64 4.4.1 (–)-Bornyl Mimic .................................................................................................... 64 4.4.2 (+)-Bornyl Mimic ................................................................................................... 72 4.4.3 Fenchyl Mimic ........................................................................................................ 79 5. References ............................................................................................................................. 91 6. 1H and 13C NMR Spectra ....................................................................................................... 96 v 1. Synthesis of 4’-Ester Resveratrol Analogues and Evaluation of Anti-cancer Activity 1.1 Introduction 1.1.1 Discovery Resveratrol (Figure 1) is a phytoalexin that was first isolated from the roots of the hellebore lily in 1940.1 It is one of many naturally occurring polyphenolic compounds typically isolated from plants. Other examples of polyphenols include genistein, equol, phloretin, isovitexin, Figure 1. Resveratrol corilagin, and epigallocatechin gallate. Resveratrol has also been found in grapes, peanuts, and soybeans in significant quantities.2 The most plentiful source of resveratrol is from the roots of Polygonium cuspidatum. Most nutritional supplements containing resveratrol are produced using extracts from these roots. Higher levels of resveratrol production can be achieved by stressing the plant through injury, exposure to ultraviolet light, or contraction of a fungal infection. The ancient Chinese and Japanese used the roots of Polygonium cuspidatum in their herbal remedies. In Asia,
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