I. synthesis, reactivity, structure and application of spiroepoxy-b-lactones: studies toward (-)-maculalactone a ii. metal mediated couplings of dichloroolefins applicable to the haterumalides
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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-b-lactones were discovered. Spiroepoxy-b-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-b-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.
Duffy, Richard Jeffrey (2007). I. synthesis, reactivity, structure and application of spiroepoxy-b-lactones: studies toward (-)-maculalactone a ii. metal mediated couplings of dichloroolefins applicable to the haterumalides. Doctoral dissertation, Texas A&M University. Available electronically from