Racemic and Enantioselective Synthesis of Cavicularin Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/wp988n13p

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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.
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  • description.provenance : Made available in DSpace on 2016-01-27T22:22:03Z (GMT). No. of bitstreams: 2 license_rdf: 1089 bytes, checksum: 0a703d871bf062c5fdc7850b1496693b (MD5) Thesis-01272016 revised.pdf: 22735975 bytes, checksum: 8aa0444d437074f83f23dea84c88b805 (MD5) Previous issue date: 2015-12-14
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  • description.provenance : Approved for entry into archive by Laura Wilson(laura.wilson@oregonstate.edu) on 2016-01-27T22:22:03Z (GMT) No. of bitstreams: 2 license_rdf: 1089 bytes, checksum: 0a703d871bf062c5fdc7850b1496693b (MD5) Thesis-01272016 revised.pdf: 22735975 bytes, checksum: 8aa0444d437074f83f23dea84c88b805 (MD5)

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