Dawson G W, Pickett J A, Smiley D W
Biological and Ecological Chemistry Department, IACR-Rothamsted, Herts., U.K.
Bioorg Med Chem. 1996 Mar;4(3):351-61. doi: 10.1016/0968-0896(96)00012-0.
Identification of a range of aphid sex pheromones as comprising the cyclopentanoids (4aS,7S,7aR)-nepetalactone, (1R,4aS,7S,7aR)-nepetalactol and the (1S)- and (1R,4aR,7S,7aS)-nepetalactols required samples authenticated by 1H and 13C NMR. These and related compounds were provided by small scale synthesis and extraction from plants in the genus Nepeta (Lamiaceae). The subsequent discovery that the synthetic sex pheromones could attract males, and also parasitic wasps that attack aphids, has created a need for large scale syntheses of the cyclopentanoids. This is afforded by cyclisation of the 8-oxo-1-enamine of citronellal as originally developed by Schreiber and co-workers (1986). Investigation into the biosynthesis of the cyclopentanoids by plants for exploiting aphid sex pheromones in crop protection by means of molecular biology required synthesis of putative biosynthetic intermediates, some with radioactive isotopic labelling, particularly 8-oxidised monoterpene alcohols and aldehydes.
鉴定一系列蚜虫性信息素，其包含环戊烷类化合物（4aS,7S,7aR）-荆芥内酯、（1R,4aS,7S,7aR）-荆芥醇以及（1S）-和（1R,4aR,7S,7aS）-荆芥醇，需要通过¹H和¹³C核磁共振鉴定样品。这些及相关化合物通过小规模合成以及从荆芥属（唇形科）植物中提取获得。随后发现合成的性信息素能够吸引雄性蚜虫，还能吸引攻击蚜虫的寄生黄蜂，这就需要大规模合成环戊烷类化合物。这可通过香茅醛的8-氧代-1-烯胺环化反应实现，该反应最初由施赖伯及其同事（1986年）开发。通过分子生物学手段研究植物中环戊烷类化合物的生物合成，以便在作物保护中利用蚜虫性信息素，这需要合成假定的生物合成中间体，其中一些带有放射性同位素标记，特别是8-氧化单萜醇和醛。
