A novel and efficient route for the synthesis of (Z)- and (E)-3-styryl-4-quinolones is described. Wittig reaction of 4-(chloroquinoline- and quinolone)-3-carbaldehydes with benzylic ylides is the key transformation for this synthetic route. The (Z)-1-methyl-3- styryl-4-quinolone is obtained with high diastereoselectivity from the reaction of 1-methyl-4-quinolone-3-carbaldehyde; while (E)-3-styryl- 4-quinolone is prepared through the Wittig reaction of 4-chloroquinoline- 3-carbaldehyde followed by acid hydrolysis. Both synthetic routes are efficient regardless of the substituents on the benzylic ylides.