Abstract
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.
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.
