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dc.contributor.advisor Hong, Jiyong en_US
dc.contributor.author Baker, Joseph B. en_US
dc.date.accessioned 2012-05-29T16:45:15Z
dc.date.available 2013-05-24T04:30:06Z
dc.date.issued 2011 en_US
dc.identifier.uri http://hdl.handle.net/10161/5702
dc.description Dissertation en_US
dc.description.abstract <p>Nature provides an abundant source of small molecules that can be used to interrogate biological systems. However, these compounds are often available in limited quantities from natural sources and must be synthesized in order to: 1) accumulate useful amounts for further study; 2) provide an efficient means to introduce structural modifications to achieve analogues. Part I demonstrates the asymmetric total synthesis of (-)-clavosolide A, showcasing the tandem allylic oxidation/oxa-Michael reaction in the stereoselective formation of the 2,3-trans-2,6-cis-tetrahydropyran core. Part II demonstrates the total synthesis of the immunosuppressive compounds, subglutinols A and B through reductive deoxygenation and cross-metathesis/intramolecular SN2&#697; reactions from a common intermediate to form the substituted 2,3-trans-2,5-trans-tetrahydrofuran and 2,3-trans-2,5-cis-tetrahydrofuran cores (subglutinol A and B respectively. Preliminary structure-activity relationships as well as biological studies are presented.</p> en_US
dc.subject Chemistry en_US
dc.subject clavosolide A en_US
dc.subject subglutinol en_US
dc.title Part 1: Total Synthesis of Clavosolide A Part 2: Total Synthesis of Subglutinols A and B en_US
dc.type Dissertation en_US
dc.department Chemistry en_US
duke.embargo.months 12 en_US

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