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(+)-(4S,5R)- and (-)-(4R,5S)-osmundalactones as well as (+)-(4R,5S)- and (-)-(4S,5R)-5-hydroxy-2-hexen-4-olides were synthesized by a concise and efficient synthesis method starting from 4-benzyloxy-5-hydroxy-2(E)-hexenoate in good yield with over 99% e.e..