The first total synthesis of both enantiomers of clavigerins B and C, insect antifeedant sesquiterpenes isolated from New Zealand liverwort Lepidolaena clavigera, has been achieved. The synthesis features Ireland-Claisen rearrangement for construction of bicyclo[3.1.1]heptene skeleton. By comparison of the optical rotations of both enantiomers with those of natural clavigerins, the absolute configurations of natural clavigerins B and C were unambiguously determined to be 1S,3S,6S,8S,9R.

中文翻译：

---

锁骨蛋白B和C的两种对映体的全合成

分离自新西兰黑麦草鳞翅目的昆虫抗饲料倍半萜烯类的锁骨蛋白B和C的对映异构体的第一全合成已经实现。该合成具有爱尔兰-克莱森重排的特征，用于构建双环[3.1.1]庚烯骨架。通过与那些自然clavigerins的两种对映体的旋光的比较，自然clavigerins B和C的绝对构型明确地确定为1小号，3小号，6小号，8小号，9 - [R 。