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Title: Towards phorboxazole B : the C20-C32 fragment
Author: Ermanis, Kristaps
ISNI:       0000 0004 5350 8414
Awarding Body: University of York
Current Institution: University of York
Date of Award: 2014
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Phorboxazole A and phorboxazole B are two potent cytostatic polyketides isolated from Phorbas marine sponge found in the Indian Ocean. Because of their excellent cytostatic activity and unprecedented structure phorboxazoles have been a very attractive target for synthetic chemists and eleven total syntheses have been reported. A novel and efficient synthesis of the C20-C32 core fragment of phorboxazoles has been developed. Key steps were: an enantioselective aldol reaction, a diastereoselective crotylation and, a diastereoselective oxy-Michael reaction. The synthesis was 7 steps long with an overall yield of 31%. A stereodivergent oxy-Michael reaction was further investigated in a computational study and analogue study.
Supervisor: Clarke, Paul A. Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available