Abstract Supellapyrone [(2R, 4R)-5-(2, 4-dimethyl)-3-methyl-2H-pyran-2-one (1)], the female sex pheromone of the brownbanded cockroach (Supella longipalpa), and its three stereoisomers were synthesized by employing lipase-catalyzed desymmetrization or enantiomer separation of syn-or anti-2, 4-dimethylpentane-1, 5-diol (9) as the key step.