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Total Synthesis of Verruculogen

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Total Synthesis of Verruculogen Part I: Synthetic Studies in Sesquiterpenes, Part II: Total Synthesis of Verruculogen A thesis presented by Dane Holte to The Scripps Research Institute Graduate Program in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the subject of Chemistry for The Scripps Research Institute La Jolla, California August 2014 ii © 2014 by Dane Holte All rights reserved iii [page # place holder for thesis acceptance form] iv Dedicated to my brother, because you’re a pretty alright brother. v Acknowledgements I have to start by acknowledging my parents, Don and Sophia, without your constant love and support over 27 years I couldn’t have made it to where I am now. Thank you both. And to Dylan: isn’t education fun? Phil, the opportunity to work in your lab, and under your guidance, has been one of the most significant events in my life. Thank you for giving me the freedom to go off on tangents and tackle the problems that I think are most intriguing, and thank you for bringing me back to the big picture and keeping me on track. To my committee, Professors Ryan Shenvi, Julius Rebek, Jin-Quan Yu, Valery Fokin, and Carlos Guerrero: thank you all for the advice over the past five years. To my undergraduate mentors: SonBinh, the ISP program truly shaped how I think about science, your advice has always been appreciated. OPP, I appreciate you giving me a summer job doing synthesis when I needed one, and supporting me when I moved to a new lab and to graduate school. Karl, and the rest of the Scheidt lab, the most important lessons I learned about doing science I picked up from you all during my last two years at Northwestern, these skills have helped carry me through graduate school. Seth Bitter, Andrew Candelaresi, and Doug Gray: I appreciate you all dealing with my infrequent emails and phone calls. I’m sorry I’ve dropped off the face of the planet. I aspire to be less busy in the future, we should hang out. Having you all as friends has been wonderful. vi Matt Beirbaum: I’m sorry, and please don’t make me say I’m sorry again, because I’m at least as, if not more, sorry than you are; and Gene Lee.com: until our next adventure, stay hungry, eat well. To my climbing partners, Jeeves, Soviet, Matt Grieving, and Matt Weiss: You’re all prolific scientists, climbers, and friends. I’d gladly let you hold me on a string a few hundred feet in the air. Climbing has kept me sane, and your various outlooks on life and science have really made me think. Kit and Nick, you were great first year roommates and Scripps hasn’t been the same without you. Your advice over the years, both chemical and otherwise, has been really helpful to me. Jamal: You’ve been a huge influence. My political awareness has been vastly improved, and my rate of recycling is at an all time high. Living with you for two years was great. Also: it gets better (or so I hear, I wouldn’t know). Erik Wold: I feel prepared to pursue an alternate career in avante garde Mexican food technology. Lets get a burrito ASAP; and Sarah: gaming with you has brought out a competitive edge that I was unaware I had. Will: When its time to party Will will party hard… and then stay up talking about science until at least 3 am. Your genuine curiosity about everything is inspiring. Brady: Scripps hasn’t been the same since u been gone. I need a home cooked meal, a belly full of beer, and a good laugh. I should also be running more. I’ve gotten fat in your absence. Hans: considering you didn’t speak to me for the first two years I was in Baran Lab, we became excellent friends. Thanks for the good music, good beers, and subtle humor. vii Dan: You brought the heat, and candy, when it was needed most; and Kanny, you and Dan continued to bring the heat. You’ve both kept me calm. Emily: You’ve been like a lab sister to me. Having you as a staple in lab for the past five years has been comforting. You’re someone I can count on, and I’m envious of your productivity; and Paul: you were a great friend inside of lab and out. I learned a lot from you during my first few years, and have always enjoyed talking about music, even when on shuffle. Brandon: Thanks for the all the adventures and going deep into cocktails with me. Yellowknife remains on the bucket list. Rejoice because you’re trying your best! Matt Villaume: You’ve helped me more than you know. LOL? Art: “Yes I like piña coladas, and getting caught in the rain…” Nathan: Your wisdom levels are high. I always appreciate your sound, sage-like advice. Steve: So long and thanks for all the booze. Florina: You are a willful woman. Rodrigo: Being hoodmates with you has been fun. I’m glad we could finish this together. Yoshi: Thanks for teaching me a lot when I first started, and thanks for keeping this ship afloat these days. Tim: Thanks for all your help during my early years. Your intelligence, productivity, and enthusiasm for chemistry is boundless. Ian: Even though I’ve tried to keep it loud, lab has been too quiet without you. Taycoh: Is it too early for a drink? Dr. Darryl David Dixon and Janice, when I die, you can have my car. This document is legally as good as a will, right? viii Shun and Abraham: I learned so much from you two, you deserve your own category. Yuki, Eddie, Yeh: I hereby apologize for being loud and obnoxious. I don’t know how you put up with me. Danny Götz: I learned more from you about doing thorough science than anyone else. Thanks so much for everything; it was truly a pleasure working, writing, and hanging out with you. Magical kugelschreiber! Jochen: I owe you a great deal of thanks, your energy kept me motivated for a final push. Feng Yu, Ippei, and Klement: it was a pleasure to work with each of you. Baran Labbers not mentioned (past and present): I’m so sorry I didn’t mention you. There are 35,436 people in this lab and you’ve all helped me a lot. Grad school has been so much fun because all the people in the lab have been like, awesome, bro. Gillian: Come down on the street and dance with me. To all my friends: None of this is going anywhere – pretty soon we’ll all be old, and no one left alive will really care about our glory days, when we sold our souls. But if you’re all about the destination, then take a flight. We’re going nowhere slowly, but we’re seeing all the sights. And we’re definitely going to hell, but we’ll have all the best stories to tell. ix TABLE OF CONTENTS Acknowledgements ..............................................................................................................v Table of Contents ............................................................................................................... ix List of Figures .................................................................................................................. xiii List of Schemes ................................................................................................................ xiv List of Tables ................................................................................................................... xvi List of Abbreviations ...................................................................................................... xvii Abstract ........................................................................................................................... xxii Part I – Synthetic Studies in Sesquiterpenes ...................................................................1 Chapter 1. Progress Toward the Total Synthesis and Transannular Cyclizations of α- Humulene .......................................................................................................................2 1.1 Background, Biosynthesis, and Cyclase Phase .................................................3 1.2 Humulene ...........................................................................................................5 1.3 Attempts at the Transannular Cyclizations of Humulene ..................................8 1.4 Progress Toward the Total Synthesis of Humulene ........................................14 1.5 Experimental ....................................................................................................31 1.6 Spectra .............................................................................................................44 Chapter 2. An Approach to Mimicking the Sesquiterpene Cyclase Phase by Nickel- Promoted Diene/Alkyne Cooligomerization ................................................................76 2.1 Introduction to Oxidative Cyclization in the Context of Terpene Synthesis ....77 2.2 Planning and Historical Context .....................................................................79 2.3 Butadiene Cooligomerizations .........................................................................85 x 2.4 Innate Reactivity of 4Z,7Z,10E-Cyclodecatrienes ...........................................94 2.5 Isoprene Cooligomerizations ...........................................................................95 2.6 Delayed Installation of C1 Units onto 4Z,7Z,10E-Cyclodecatriene 2.20c .......99 2.7 Conclusion .....................................................................................................101 2.8 Experimental .................................................................................................111 2.9 Spectra ...........................................................................................................137 Chapter 3. Macrocyclic Sesquiterpenes: The Fallout ................................................294 3.1 On the Mechanism, Reactivity,
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