【摘要】 <正> 顺-9-十四碳烯-1-醇乙酸酯（1）是鳞翅目许多昆虫的性信息素或其组分之一。已报道的化合物1的合成方法是采取C₁₀+C₄或C₉+C₅偶联原则。本文报道另一条合成路线（图1）,采取C₈+C₆原则,以1,8-辛二醇（2）为原料,经过ω-氯代辛醇（3）得2-（8′-氯辛烷-1-氧基）四氢吡喃（4）^[2d],卤代物4与己炔-1（5）的锂盐缩合得炔化物6,然更多还原

【Abstract】 The title compound （1）, the major compound of insect sex pheromone of summer tortrix moth （Adoxophes orana F. von R.）was synthesized in 5 steps with a 40％ overall yield according to the C₈+ C₆ coupling principle, using 1, 8-octandiol as starting material. Namely, coupling of lithium salt of hexyne-1 with 2- （8’-chlorooctyloxy-） tetrahydropyrane gave 2-（9’-tetradecyloxy-）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.更多还原