Dong, Ping, authorWood, John Louis, advisorWilliams, Robert M., committee memberRovis, Tomislav, committee memberBernstein, Elliot R., committee memberPartin, Kathryn M., committee member2007-01-032007-01-032011http://hdl.handle.net/10217/47380Two synthetic approaches towards cephalezomine A and phomoidride D are described separately. The first approach towards cephalezomine A invented a new method for the synthesis of 3-butoxy-1-chlorobutenone and successful constructed α-O and ß' -N disubstituted dienone for a designed key intermediate of cascade cyclization by Eschenmoser coupling of thiolactam and 3-butoxy-1-chlorobutenone. The second approach towards phomoidride D systematically studied the electronic effects of different ester substituents for the phenolic oxidation and inverse electron demand Diels-Alder reaction, which resulted in the synthesis of functionalized bicyclic [2.2.1] intermediate. Base on this, a new route for the synthesis of precursor of Grob fragmentation has been established towards the total synthesis of phomoidride D by samarium diiodide mediated radical cascade cyclization.born digitaldoctoral dissertationsengCopyright and other restrictions may apply. User is responsible for compliance with all applicable laws. For information about copyright law, please see https://libguides.colostate.edu/copyright.Eschenmoser couplingsynthetic approachsamarium diiodide mediated radical cascade cyclizationphenolic oxidation and Diels-Alder reactionphomoidride Dcephalezomine AText