A versatile strategy for the synthesis of 2,6-disubstituted dihydropyranones

(Chemical Equation Presented) A concise synthesis of 2,6-disubstituted dihydropyranones was developed. This sequence is based on the Smith three-component dithiane linchpin coupling strategy. By simply switching the order of epoxide addition in the linchpin coupling step, two analogous dihydropyranones were prepared in good yield from the same starting materials. This sequence allows for considerable flexibility in the nature of R₁ and R₂ groups, which facilitates the preparation of a diverse array of 2,6-disubstituted dihydropyranones.