Catalytic divergent synthesis of quinazolinone alkaloids

Thesis

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.

Authors: Wei, T

• DOI: 10.5287/ora-dakeq0gdj
• Type of award: DPhil
• Level of award: Doctoral
• Awarding institution: University of Oxford