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Title: The enantioselective synthesis of (-)-Luminacin D
Author: Bartlett, Nathan
ISNI:       0000 0004 2748 085X
Awarding Body: University of Southampton
Current Institution: University of Southampton
Date of Award: 2012
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Luminacin D, isolated from the fermentation broth of soil bacterium Streptomyces sp. Mer-VD1207, has angiogenesis inhibitory activity. In vivo studies have shown this activity derives from a novel mode of action, thus making luminacin D an interesting target for synthesis. Previous syntheses have not enabled the preparation of the spiro-epoxypyran moiety in a stereoselective manner, and luminacin D has been isolated as a mixture with the 6’,8’ – epimer as a result. This has been overcome by early, stereospecific introduction of the epoxide in our synthesis and we have constructed the natural product skeleton with the correct absolute stereochemistry, by chelation controlled diastereoselective additions. This has enabled possibly the first enantioselective and diastereoselective synthesis of this natural product to be completed. The allylation of α-heteroatom substituted aldehydes was of significance to the synthesis as the key step in the synthesis involved allylation of an α-epoxyaldehyde. These allylation reactions have been investigated by DFT calculations to unambiguously assign the Evans-Conforth and Polar Felkin-Ahn models in these additions.
Supervisor: Linclau, Bruno Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry