(Hetero)-aryl ketones derivatives with antibacterial properties
Conformationally restricted aryl and heteroaryl ketones derived from monic acid have useful antibacterial properties.
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(2008/06/13)
Preparation of E-(2-substituted-1-methylethylidene)indanones derived from monic acid
Alkylation of the lithium dienolate of the monic acid hydroxamate (3) with o-bromo(bromomethyl) benzene or heteroaromatic derivatives gave α-alkylated products (5). This alkylation procedure was surprisingly catalysed by 4- dimethylaminopyridine. Metal-halogen exchange with t-butyl lithium occurred with concomitant intramolecular cyclisation to give a mixture of the deconjugated ketones (6). Reconjugation with potassium t-butoxide stereoselectively produced the E-isomer (7). Deprotection gave the monic acid derived ketone (1).
Pearson, Neil D.,Broom, Nigel J.P.,O'Hanlon, Peter J.
p. 3771 - 3774
(2007/10/02)
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