I. synthesis, reactivity, structure and application of spiroepoxy-b-lactones: studies toward (-)-maculalactone a ii. metal mediated couplings of dichloroolefins applicable to the haterumalides

• Main Author: Duffy, Richard Jeffrey
• Other Authors: Romo, Daniel
• Format: Others
• Language: en_US
• Published: 2010
• Subjects: Total Synthesis; Natural Products
• Online Access: http://hdl.handle.net/1969.1/ETD-TAMU-2444; http://hdl.handle.net/1969.1/ETD-TAMU-2444

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.