Graduate Thesis Or Dissertation
 

Racemic and Enantioselective Synthesis of Cavicularin

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  • This dissertation describes the racemic and enantioselective synthesis cavicularin. Cavicularin is a macrocyclic bisbibenzyls family member natural product. It has been an attractive synthetic target due to its intriguing structure: the macrocyclic core imparts sufficient strain on the system to force one benzene rings to adopt a boat-shaped conformation, out of planarity for about 15°. The natural product also exhibits optical activity though containing no stereocenters. The restricted biaryl bond rotation in this molecule results in conformational chirality. A review of cavicularin macrocyclic bisbibenzyls is discussed, including isolation, biological activity and existing synthetic routes. The racemic synthesis of cavicularin featuring a Diels-Alder-retro-Diels-Alder cascade to build the bent benzene ring is discussed. A cinchona alkaloids catalyzed Diels-Alder reaction is used to synthesize cavicularin enantioselectively. A one-pot three-component Suzuki coupling reaction is employed to build the terphenyl core in cavicularin rapidly. The Suzuki coupling reaction is further developed to broaden the substrate scope and a proteomimetic target was prepared to showcase this methodology. A synthetic approach towards bazzanin K, which is another macrocyclic bisbibenzyls compound, is covered.
  • Keywords: Natural product, Total synthesis, Cavicularin
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file details Thesis-01272016_revised.pdf 2017-08-07 Pubblico Scaricare