The 9-azabicyclo[3.3.1]nonane ring system is present in several insect- and plant-derived alkaloids. (−)-Adaline (1) and (+)-euphococcinine (2), found in secretions of Coccinelid beetles, and (+)-N-methyleuphococcinine (3), isolated from the Colorado blue spruce Picea pungens, are members of this alkaloid family. Their unique bicyclic system with a quaternary stereocenter, and the potent biological activity exerted by these homotropane alkaloids, make them attractive synthetic targets. This work aims briefly to review the chemical ecology of Adalia bipunctata and the recent methodologies to obtain adaline (1), euphococcinine (2), and N-methyleuphococcinine (3).

中文翻译：

---

合成高辛烷生物碱adaline，大果球菌碱和N-甲基大果球菌碱的最新进展

9-氮杂双环[3.3.1]壬烷环系统存在于几种昆虫和植物来源的生物碱中。（ - ） - Adaline的（1）和（+） - euphococcinine（2），在分泌物中发现Coccinelid甲虫，和（+） - ñ -methyleuphococcinine（3）中，从科罗拉多蓝色云杉分离云杉，是这种构件生物碱家族。它们独特的具有四级立体中心的双环系统，以及这些高辛烷生物碱所发挥的强大生物活性，使其成为有吸引力的合成靶标。这项工作的目的是简要回顾一下Adalia bipunctata的化学生态学以及最近获得adaline（1），euphococcinine（2）和N-甲基大磷球菌碱（3）。