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Title: Catalytic divergent synthesis of quinazolinone alkaloids
Author: Wei, Tao
ISNI:       0000 0004 7654 7352
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2019
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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. Chapter 1 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. Chapter 2 demonstrates our first-generation catalytic divergent synthetic approach towards both tryptoquivaline F and chaetominine. Chapter 3 mainly illustrates the second-generation total synthetic approach towards tryptoquivaline F. Chapter 4 shows our total synthesis work on a naturally occurring pentacyclic quinazolinone natural product and core of tryptoquivalines, followed with homologations towards tryptoquivaline F.
Supervisor: Dixon, Darren J. Sponsor: China Scholarship Council
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available