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TOWARDS PHORBOXAZOLE B: THE C20-C32 FRAGMENT

Ermanis, Kristaps (2014) TOWARDS PHORBOXAZOLE B: THE C20-C32 FRAGMENT. PhD thesis, University of York.

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Abstract

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.

Item Type: Thesis (PhD)
Academic Units: The University of York > Chemistry (York)
Depositing User: Mr Kristaps Ermanis
Date Deposited: 03 Feb 2015 12:53
Last Modified: 01 Oct 2016 00:18
URI: http://etheses.whiterose.ac.uk/id/eprint/7823

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