The Synthesis of (±)-Patulolide C and its Epimer Via Dodec-3-En-11-Olide

Abstract A novel route to dodec-3-en-ll-olide 3, a macrolide pheromone of cucujid grain beetles is reported. Compound 3 provides an access to the antimicrobial (±)-patulolides and (±)-epipatulolide C. Conformational restrictions hamper the rearrangement of the 12-membered βγ-epoxylactones 7 to corresponding allylic alcohols 2.