Both (5S,7S)- and (5R,7S)-isomers of kurzilactone were synthesized from a 'chiral epoxy-aldehyde synthon' through the coupling of an acyl anion equivalent and the dianion of acetoacetate, followed by formation of the Kawa-type lactone by cyclization and elimination. Comparing the spectral data of the synthesized and naturally occurring kurzilactone, the C(5)- and C(7)-stereogenic centers of the natural kurzilactone was assigned a corrected anti-relationship with (5R,7S)-absolute configuration.