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.
| Identifer | oai:union.ndltd.org:tamu.edu/oai:repository.tamu.edu:1969.1/ETD-TAMU-2444 |
| Date | 15 May 2009 |
| Creators | Duffy, Richard Jeffrey |
| Contributors | Romo, Daniel |
| Source Sets | Texas A and M University |
| Language | en_US |
| Detected Language | English |
| Type | Book, Thesis, Electronic Dissertation, text |
| Format | electronic, application/pdf, born digital |
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