Magnus, Philip D.1569437422008-08-282008-08-282006http://hdl.handle.net/2152/2797textStudies directed towards the total synthesis of the cytotoxic ent-kaurane diterpene irroratin A were carried out. In a model system it was found that Pummerer cyclization gave a bicyclo[2.2.2]octane whereas activation as an allylsilane gave the desired [3.2.1]- bicycle. In a more functionalized system, the use of a rhodium-catalyzed C-H insertion reaction allowed for ready access to the bicyclo[3.2.1]octan-6-one core structure. Attempts to construct the remainder of irroratin A utilizing this core structure were ultimately unsuccessful. The use of a Nazarov reaction for the diastereoselective synthesis of silvestrol and rocaglamide was also studied. A model compound lacking the 6,8-oxygenation present in the natural products was synthesized and subjected to a variety of Lewis and Brønsted acids; in all cases no Nazarov cyclization was observed, but rather (typically) retro Friedel-Crafts acylation. In an attempt to bias the reaction towards the desired pathway more activated substrates were made; however, cyclization was again unsuccessful.electronicengCopyright is held by the author. Presentation of this material on the Libraries' web site by University Libraries, The University of Texas at Austin was made possible under a limited license grant from the author who has retained all copyrights in the works.Irroratin A--SynthesisRocaglamide--SynthesisSilvestrol--SynthesisThesis