배추좀나방의 성 페로몬을 새로운 방법으로 합성하여 EAG감응반응을 수행하였다. 프로파길알코올의 이중음이온을 알킬화하여 2-도데신-1-올을 얻고 이를 아세틸렌-지퍼반응에 의해 11-도데신-1-올로 전환시킨 다음, 다시 이중음이온 알킬화반응에 의해 11-헤사데신-1올을 얻었다. 이를 수소환원시켜 (Z)-11-헥사데센-1-올 (3)을 얻었고 이 알코올을 산화시켜 (Z)-11-헥사데센-1-알(1)을, 아세틸화시켜 (Z)-11-헥사데센-1-일 아세테이트(2)를 각각 얻었다. 이렇게 합성하여 얻어진 화합물 각각 또는 혼합물에 대해 배추좀나방의 ESG감응반응을 측정하였다.
New synthesis and electroanthennogram (EAG) responses of the pheromones of the diamond back moth Plutella xylostella L. are described. Lithium dianion of propargyl alcohol was alkylated with 1-bromononane to give 2-dodecyn-1-ol, which was converted to 11-dodecyn-1-ol by acetylene-zipper reaction. Dianion of 11-dodecyn-1-ol was alkylated with 1-bromobutane to provide 11-hexadecyn-1-ol, which was in turn reduced over Pd/BaSO4 to afford (Z)-11-hexadecen-1-ol (3). (Z)-11-Hexadecen-1-ol was oxidized and acetylated to (Z)-11-hexadecen-1-al (1) and (Z)-11-hexadecen-1-yl acetate (2), respectively. The electroantennogram (EAG) responses of the diamond back moth to the pheromone compouds thus synthesized were measured.
