Total Synthesis of Loline Alkaloids and Studies toward Naphthomycin K

264 Pages·2012·15.84 MB·English

by  Mesut Cakmak

Dissertation zur Erlangung des Doktorgrades
der Fakultät für Chemie und Pharmazie
der Ludwig-Maximilians-Universität München

Total Synthesis of Loline Alkaloids
and Studies toward Naphthomycin K

vorgelegt von
Mesut Ҫakmak
aus München, Deutschland

2012

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Erklärung:
Diese Dissertation wurde im Sinne von § 7 der Promotionsordnung vom 28.
November 2011 von Herrn Prof. Dr. Dirk Trauner betreut.

Eidesstattliche Versicherung
Diese Dissertation wurde eigenständig und ohne unerlaubte Hilfe erarbeitet.

München, den 11. Juni 2012

(Mesut Ҫakmak)

Dissertation eingereicht am 11. Juni 2012
1. Gutachter: Prof. Dr. Dirk Trauner
2. Gutachter: Prof. Dr. Konstantin Karaghiosoff
Mündliche Prüfung am 11. Juli 2012

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Alles Gescheite ist schon gedacht worden, man muss nur versuchen, es noch einmal
zu denken.
Johann Wolfgang von Goethe

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Acknowledgement

I would like to first and foremost thank my advisor and mentor, Prof. Dr. Dirk Trauner.
Joining the group as his first PhD student at the LMU München was truly a special
experience. His enthusiasm for and encyclopedic knowledge of both chemistry and
general science has been a constant source of motivation and crucial for the success
of my projects. I especially appreciated his trust in my work and the freedom he
granted me to explore new ideas and solve problems at hand.
Thanks to Prof. Dr. Karaghiosoff for appraising my dissertation.
And thanks to Prof. Dr. Hoffmann-Röder, Prof. Dr. Bracher, Prof. Dr. Langhals and
Prof. Dr. Heuschmann for being available as examiners in my defense.
I would like to thank my wife Aylin, who is “solid as rock” in my life. She constantly
supported and motivated me since I met her for the very first time. Such a
performance would have been not possible without her wonderful character, her
patience and her immense understanding. You have given this work and my life great
meaning. I love you!
I owe my family so much that I don’t even know where to start. Their support during
my whole education is the reason why I made it this far. My parents believed in
providing me with the best possible education no matter the sacrifice. I cannot thank
them enough for their unconditional love.
I’d like to thank my uncle Mümtaz for his guidance in educational questions.
Upon spending most of my time in the laboratory, I quickly learned the true value of
my labmate and close friend Christian A. (A like awesome) Kuttruff. He truly had a big
impact on my dissertation. His help in computational issues, discussions about
chemistry and private life, exchange of ideas, squash games, going on vacation
(Huttanz!) and his good taste in music made my PhD very enjoyable.
Special thanks go to all my labmates from the Trauner group, namely Jennifer Lachs,
Ingrid Chen, T. J. Kimbrough, Anastasia Hager, Christian A. Kuttruff and Elena
Herrero-Gómez, for being good colleagues and creating a nice and peaceful lab
atmosphere. Further, I would like to acknowledge, Eddie Myers, Robert Webster,
David Woodmansee, Julien Lefranc and Christian A. Kuttruff for their help proof-
reading applications, publication manuscripts and this dissertation.
Thanks also to Arunas Damijonaitis and Julien Lefranc for taking over my projects.
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I also like to thank all the other members of the Trauner group, Laura Salonen, Laura
Laprell, Tatsuya Urushima, Katie Abole, Dmitry Mazunin, Boris Gasper, Maria
Matveenko for handing me over the oil pump group job, Martin Olbricht for his
delicious wedding cake, Irina Albrecht inviting me to her wedding, Vilius
Franckevicius for super Denksport explanations, Giulio Volpin for making fun of
others, Timm Fehrentz for having a good time in our last Praktikum, Robert Webster
for teaching me squash, Simon Geiger for his support in the naphthomycin project,
Sebastian Strych for discussions about chemistry, Matthias Schönberger for joining
adventure activities, Johannes Broichhagen for his continuous visits of lab exile,
Florian Löbermann for his dinner invitation, Anastasia Hager for borrowing her pc for
pymol videos, Albert Schröckeneder for showing me how to tinker an alu-rose, Eddie
Myers for exotic Denksports, Michael Kienzler for having Döner-sessions before
going to the gym, Vladimir Sofiyev for being vladcore, Holger Moroder for his
introduction about self-assembly, Jan Schwarz for having workouts at 7 am, Julian
Egger for playing Bushido all day long, Michael Pangerl for demonstration of big-
scale reactions, T. J. Kimbrough for teaching me how to do pipette columns, David
Woodmansee for giving awesome talks, Desiree Stichnoth for joining our soccer
games, Jennifer Lachs for her funny sneezing, Ingrid Chen for talking about long-
distance relationships, Elena Herrero-Gómez for giving me hints for the ICIQ
summerschool, Marco Stein for helping me to matriculate, Pascal Ellerbrock for
taking over my groupjob, Alwin Reiter for our chats about scuba diving, Dominik
Hager for showing me the ozon generator, Daniel Hog for organizing soccer games,
Florian Huber for chatting about bodybuilding, Philipp Stawski for his help in making
my poster, Harald Janovjak for chatting about boxing and all together for creating
such a professional, educational and enjoyable work environment.

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I’d like to express my gratitude to the people who made my dissertation possible:
Staff from the Trauner Group: Tobias Kauer, Petra Böhrer, Carrie Louis, Dr. Martin
Sumser and especially Heike Traub for being supportive in all kind of bureaucratic
issues;
Staff from the LMU Analytic department: Dr. Spahl and Frau Kosak for mass
spectroscopic data, Dr. Stevenson and Fr. Dubler for NMR data and especially Dr.
Mayer for his patience and efforts in finding suitable crystals for x-ray analysis.
I am also grateful to many teachers that fostered my interest in organic chemistry.
These people include Frau Engelberger, Frau Geisler, Dr. Dimitrios Mihalios, Dr.
Sebastian Brandes, Dr. Birte Basler, Dr. Roger Norcross, Prof. Thorsten Bach and
Dr. Herbert Schuster.
I’d like to thank Bastian Sauerer for having funny pizza dinners with progress reports.
During my PhD studies I had the joy to supervise a number of very motivated
undergraduate co-workers, who spend a lot of time with me in the lab and were all
very hard-working: Sebastian Götte, Christine Sturm, Ufuk Borucu, Caroline Pflüger,
Christine Hieke, Ebru Zeynep Serdar, Andreas Ahlers, Hiroki Nakatsu, Johannes
Feierfeil and Klaus Speck. Thank you all for being so supportive.
Last but not least, special thanks go to my close friends Ömer Özcan (Bergtürke),
Akram Barkia (Camel) and Zoran Pranjic (RedNinja), who have been as supportive
as friends can possibly be and challenged me in go-cart races, wakeboarding and
rafting.

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This dissertation is dedicated to my father.

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