The title compound (1),the mayor oompound of insect seg pheromone of summer tortrig moth (Adoxophes orama F.von R.) was synthesized.in 5 steps with a 40% overall yield according to the C₈+C₆ coupling principle,using 1,8-ootandiol as starting material.Namely,coupling of lithium salt of hexyne-1 with 2-(8^*chloroocstyloay-)tetra-hydropyrane gave 2-(9'-tetradeoylogy-) tetrahydropyrane,which was partially hydrogenated in the presence of Lindlar catalyst to form compound 7.Simultaneous deprotection and acetylation of 7 with acetyl chloride and acetic acid afforded the title compound 1.The isomeric purity of compound 1 was about 98% as shown by gas chromatography.The E isomer 9 was also synthesized from 6 by means of sodium-liquid ammonia reduction followed by acetylation.