Copper and cobalt mediated regioselective alkylation of polyketide models: Methyl 3,5-dioxohexanoate and triacetic acid lactone

Article abstract of DOI:10.1016/S0040-4020(01)89770-2

Regioselective C-alkylations at the intercarbonyl positions C-4 and C-2 of the polyketide model methyl 3,5-dioxohexanoate, 1, have been acomplished through reactions of its cobalt(II), 4a, and copper(II), 4b, complexes respectively. Some examples of double alkylations at both positions are presented. Cyclizations of the regioselectively substituted diketoesters so prepared gave triacetic acid lactone derivatives regioselectively alkylated at C-5 and at C-3.