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Total Asymmetric Synthesis of Ring-A Derivatives of (+)-Trans-Dihydronarciclasine

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Total Asymmetric Synthesis of Ring-A Derivatives of (+)-Trans-Dihydronarciclasine M. Sc. Thesis – J.R. Scattolon; McMaster University – Chemical Biology TOTAL ASYMMETRIC SYNTHESIS OF RING-A DERIVATIVES OF (+)-TRANS-DIHYDRONARCICLASINE M. Sc. Thesis – J.R. Scattolon; McMaster University – Chemical Biology TOTAL ASYMMETRIC SYNTHESIS OF RING-A DERIVATIVES OF (+)-TRANS-DIHYDRONARCICLASINE By JON R. SCATTOLON, H. B. Sc. A Thesis Submitted to the School of Graduate Studies in Partial Fulfilment of the Requirements for the Master of Degree Master of Science McMaster University © Copyright by Jon R. Scattolon, November 20 M. Sc. Thesis – J.R. Scattolon; McMaster University – Chemical Biology M.Sc. Thesis (2020); McMaster University, Hamilton Ontario – Chemistry TITLE: Total asymmetric synthesis of ring-A derivatives of (+)-trans- dihydronarciclasine. AUTHOR: Jon R. Scattolon, H. B. Sc. Minor Physics (Brock University). SUPERVISOR: Professor James McNulty. PAGES xvii, 181. ii M. Sc. Thesis – J.R. Scattolon; McMaster University – Chemical Biology Lay Abstract This thesis is primarily driven towards the development of four antiviral lycorane structural type alkaloids, and an analogue synthesized via a copper-cocatalyzed Sonogashira reaction, utilizing a labile phenol-derived sulfonated hydroxyl group in its coupling towards an alkyne tagged structure. This method provides easy access for a variety of compounds without a fluorescent tag, taking steps forward in elucidating how the Amaryllidaceae alkaloids are delivering their biological effects. The densely substituted ring-C was obtained via an asymmetric organocatalytic [3+3] sequence for the assembly of the aminocyclitol core and is described. This sequence has provided effective regio, diastereo, and enantioselective access to five unnatural products. Preparation of the precursors were prepared using a Wittig methodology previous reported by the McNulty group that has been used in many syntheses for various Amaryllidaceae alkaloids. iii M. Sc. Thesis – J.R. Scattolon; McMaster University – Chemical Biology Abstract Significant attention from the medicinal and pharmaceutical communities has been pushed towards the design and development of natural products for defence against many forms of illnesses. The Amaryllidaceae plant family has shown their prevalence over time aiding towards our needs and becoming viable sources of alkaloids due to their wide variety of bioactivities presented. The low availability towards these often-complex structures with at times comprising up to six contiguous chiral centers have made practical testing scarce. More dominantly the isocarbostyrils are well recognized, being hydroxylated phenanthridones providing increased activities making them model targets to test and develop new synthetic strategies towards. These compounds represent a subset of the Amaryllidaceae alkaloids that lack a basic nitrogen center. This thesis describes the total synthesis of four derivatives of the antiviral natural product (+)-trans-dihydronarciclasine from α-azidoacetone and m-anisaldehyde. Herein we demonstrate constructive routes towards ring-A modified, fully functionalized rings-B/C derivatives synthesized via asymmetric chemical syntheses providing further insight into SAR studies. This thesis expands on the organocatalytic [3+3]-cycloaddition sequence to produce aminocyclitol cores providing effective routes towards the development of five stereogenic centers in all targeted ring-C structures. Such studies were attributed to the enal adducts isolated from the Wittig reaction towards four natural product derivatives gaining knowledge related to the targeted molecules mode of action. One additional (+)-trans- dihydrolycoricidine analogue will be communicated, that enables the imaging while inside live cells with use of alkyne-tag Raman imaging. iv M. Sc. Thesis – J.R. Scattolon; McMaster University – Chemical Biology Limitations of the alkaloids include the toxicity that accompanies these agents and the poor aqueous solubilities they provide, eliciting an increased need for new antiviral agents. The syntheses communicated provide effective routes towards unnatural alkaloids and can be pushed towards alternative chiral aminocyclitol targets for future studies. All compounds have been sent away for screening including against coronavirus at Johns Hopkins. v M. Sc. Thesis – J.R. Scattolon; McMaster University – Chemical Biology Acknowledgements I would like to start by thanking Dr. Jim McNulty for his long-standing experience and growth as a chemist I have gained over the years. From volunteering all the way to completing my Master’s it has been my great honor and privilege to do so by his side. His encouragement and motivation has helped me push farther along the way. Learning from such a motivated and driven leader has only kept me focused. I would also like to thank my committee members Dr. Paul Harrison and Dr. Philip Britz-McKibbin for their guidance and feedback related to my work over the years, helping me on improving and giving me valuable words of advice every meeting. Their words of advice were always applied, preparing myself for the next steps I was to face in completing this milestone in my life. Additionally, I will always appreciate my colleague’s assistance throughout my studies, helping me develop a deeper understanding when applying new techniques and helping when asked. A more notable mention to my friend and colleague Chanti for being apart of multiple total syntheses related to natural product derivatives these past few years, it has been a growing experience and I look forward to continuing where I left off. Grateful towards my family and girlfriend for their much-loved support, and I already can hear my mother saying “you got it from me not your father” so I’ll have my smile and nod reaction ready don’t you worry. vi M. Sc. Thesis – J.R. Scattolon; McMaster University – Chemical Biology Table of Contents Lay Abstract ...................................................................................................................... iii Abstract ............................................................................................................................. iv Acknowledgements ........................................................................................................... vi Table of Contents ............................................................................................................. vii List of Figures .................................................................................................................... x List of Tables .................................................................................................................. xiii List of Schemes .................................................................................................................. x List of Abbreviations and Symbols ................................................................................. xiv Declaration of Academic Achievement .......................................................................... xvii 1. Introduction ……………………………………………………………………………. 1 1.0.1 References ………………………………………………………………….. 2 1.1 Amaryllidaceae plant family History ...………………………………………………. 3 1.1.1 References ………………………………………………………………… 15 1.2 Discovery and Biosynthesis ………………………………………………………..... 22 1.2.1 References ……………………………………………………………….... 27 1.3 Antiviral Activities from Amaryllidaceae Alkaloids and Their Analogues …..……... 28 1.3.1 References ……………………………………………………………….... 30 1.3A Antiviral Studies by Gabrielsen et. al. in 1992 ………………………………..…... 32 1.3A.1 References …………………………………………………………..…... 38 1.3B Antiviral Studies by Kobayashi et. al. in 1989 …………………………………...... 38 1.3B.1 References …………………………………………………………..…... 40 1.3C Antiviral Studies by McNulty et. al. in 2016 …………………………….………... 41 1.3C.1 References ……………………………………………………………..... 42 1.3D Antiviral Studies by McNulty et. al. in 2018 ………………………….…………... 42 vii M. Sc. Thesis – J.R. Scattolon; McMaster University – Chemical Biology 1.3D.1 References ………………………………………………………..……... 44 1.4 First Isolation, Biological Activities, and Syntheses ..………………………….….... 44 1.4A (+)-Narciclasine …………………………………………………………………. 45 1.4A.1 References ………………………………………………………………. 49 1.4B (+)-trans-Dihydronarciclasine ……………………………………………..……. 50 1.4B.1 References ………………………………………………………..……... 53 1.4C (+)-Lycoricidine …………………………………………………………..…….. 54 1.4C.1 References …………………………………………………………..…... 56 1.4D (+)-Pancratistatin ……………………………………………...………………… 56 1.4D.1 References …………………………………………………………..…... 59 1.4DD Selected Total Synthesis of (+)-Pancratistatin …………………………..…….. 61 1.4DD.1 References ……………………………………………………..….…... 65 1.5 Banwell’s modification of the Bischler-Napieralski reaction ……………………..... 66 1.5.1 References ……………………………………………………………….... 71 1.6 Copper-Catalyzed Sonogashira Reaction ………………………………………...… 72 1.61 References ……………………………………………………………...…. 86 2.0 Thesis Introduction ……………………………………………………………….... 91 2.01 References ……………………………………………………………...…. 97 2.1 Synthesis and Functionalization of Ring-C ………………………………….……. 100 2.11 Conclusion ………………………………………………………..……… 109 2.12 Experimental ……………………………………………………….……. 111 2.12.1 References ……………………………………………………….…….. 122 viii M. Sc. Thesis – J.R. Scattolon; McMaster University – Chemical Biology 2.2 Total Synthesis of Four (+)-trans-Dihydronarciclasine Derivative Targets ..…...…. 123 2.21 Conclusion ……………………………………………………….………. 126 2.22 Experimental ……………………………………………………………... 127 2.22.1 References ………………………………………………………..…….. 133 2.3
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