p-Methoxybenzyl itaconate (III) was prepared by reaction of itaconic anhydride (I) with p-methoxybenzyl alcohol (II) at 55-60 C (1). Condensation of the lithium enolate of (III) with nonanal (IV) in THF at -78 C gave adduct (V), which upon treatment with trifluoroacetic acid underwent cyclization and benzyl ester deprotection to yield the corresponding butyrolactone as a diastereomeric mixture. The major trans isomer was finally isolated by flash chromatography.