δ-Hydroxy-β-keto esters and δ,β-dihydroxy esters are characteristic structural motifs of statin-type natural products and drug candidates. Here, we describe the synthesis of functionalized δ-hydroxy-β-keto esters in good yields and excellent enantioselectivities using Chan's diene and modified Mukaiyamaaldol reaction conditions. Diastereoselective reduction of δ,βdihydroxy esters afforded the respective syn- and anti-diols, and saponification yielded the respective acids. All products were evaluated for their anti-inflammatory properties, which uncovered a surprising structure-activity relationship.