http://www.loc.gov/mods/v3 http://www.loc.gov/standards/mods/v3/mods-3-2.xsd
I. Synthesis, reactivity structure and application of spiroepoxy-[beta]-lactones
studies toward (-)-maculalactone A II. Metal mediated couplings of dichloroolefins applicable to the haterumalides
Marine natural products have continued to be a source of compounds with interesting structures and biological activities. Two such compounds are maculalactone A and haterumalide NA. In the process of exploring a route to the synthesis of haterumalide NA, the novel ring system, spiroepoxy-[beta]-lactones were discovered. Spiroepoxy-[beta]-lactones were synthesized by the oxidation of ketene-homo dimers with dimethyldioxirane (DMDO). After a synthetic route to this ring system was obtained we next explored the varied reactivity of spiroepoxy-[beta]-lactones, and it was apparent that they might be applied to the synthesis of maculalactone A. Also with the aim of the total synthesis of the haterumalides, a palladium catalyzed cross coupling was developed. This reaction couples a 1,1-dichloroolefin with an alkyl zinc reagent. It was found that this reaction necessitates a heteroatom on the zinc reagent in order to proceed.
Title from author supplied metadata (automated record created 2010-03-12 12:08:51).
Doctor of Philosophy Texas A&M University 2007 http://hdl.handle.net/1969.1/ETD-TAMU-2444