COPPER COMPLEX PROTECTION IN THE REGIOSELECTIVE ALKYLATION OF METHYL 3,5-DIOXOHEXANOATE. PREPARATION OF 3-ALKYL DERIVATIVES OF 4-HYDROXY-6-METHYL-2-PYRONE

Article abstract of DOI:10.1016/S0040-4039(00)96365-2

Protection of the diketone moiety of the polyketide model methyl 3,5-dioxohexanoate by copper(II) complex formation followed by alkylation of the free C-2 position results in overall regioselective alkylation of the diketoester to afford methyl 2-alkyl-3,5-dioxohexanoates, which under cyclization afford 3-alkyl derivatives of triacetic acid lactone.