Abstract
Oligomethylene-tethered ω-alkenyl 3-oxobutanoates and 3-oxobutanamides underwent manganese(III)-mediated oxidative intramolecular addition to produce dihydrofuran-fused macrolides and macrocyclic amides from 8 to 26 members. A similar reaction of the oligooxamethylene-tethered ω-alkenyl 3-oxobutanoates also gave dihydrofuran-fused crown ether type macrolides which had a phase-transfer ability with sodium and potassium pi-crates. The manganese(III)-assisted specific intramolecular addition could be explained by the π-complexation of the ω-alkenyl part with the manganese(III) enolate.
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