I. synthesis, reactivity, structure and application of spiroepoxy-b-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-b-lactones...
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| Format: | Others |
| Language: | en_US |
| Published: |
2010
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| Online Access: | http://hdl.handle.net/1969.1/ETD-TAMU-2444 http://hdl.handle.net/1969.1/ETD-TAMU-2444 |
| Summary: | 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. |
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