Catalytic divergent synthesis of quinazolinone alkaloids
<p>The general goal of this thesis was to implement a new, catalytic, enantioselective isocyanoacetate ketone aldol reaction into a challenging total synthesis plan, in order to achieve a catalyst controlled stereoselective total synthesis of a specific subset of quinazolinone alkaloids - tryp...
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| Format: | Thesis |
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2019
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| Summary: | <p>The general goal of this thesis was to implement a new, catalytic, enantioselective isocyanoacetate ketone aldol reaction into a challenging total synthesis plan, in order to achieve a catalyst controlled stereoselective total synthesis of a specific subset of quinazolinone alkaloids - tryptoquivalines and chaetominine.</p> <p><b>Chapter 1</b> firstly introduces the panorama of quinazolinone alkaloids and pioneering synthetic achievements on tryptoquivalines and chaetominines. Subsequently, previous crucial development of isocyanoacetate ester aldol/Mannich reactions were concisely reviewed.</p> <p><b>Chapter 2</b> demonstrates our first-generation catalytic divergent synthetic approach towards both tryptoquivaline F and chaetominine.</p> <p><b>Chapter 3</b> mainly illustrates the second-generation total synthetic approach towards tryptoquivaline F.</p> <p><b>Chapter 4</b> shows our total synthesis work on a naturally occurring pentacyclic quinazolinone natural product and core of tryptoquivalines, followed with homologations towards tryptoquivaline F.</p> |
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