Tetrahedron Letters p. 3771 - 3774 (1994)
Update date:2022-08-03
Topics:
Pearson, Neil D.
Broom, Nigel J.P.
O'Hanlon, Peter J.
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).
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