A stereoselective synthesis of (±)-malyngolide

Abstract

A stereoselective synthesis of (±)-malyngolide(1) has been accomplished by applying a cross-aldol condensation of the dianion of ethyl 2-methyl-3-oxobutyrate (3) with 1-(tetrahydropyran-2-yloxy)-undecan-2-one (4). Reduction of the 3-oxo group of the resulting 3-oxopentanolide (6), followed by dehydration of the alcohol (7) and catalytic hydrogenation of the unsaturated hydroxy lactone (10), furnished (±)-malyngolide (1) in 34% overall yield.