Zhu Meng, Liu Xiao-Yu, Chen Qiao-Hong, Wang Feng-Peng
Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, Chengdu, 610041, China.
J Asian Nat Prod Res. 2012;14(5):441-9. doi: 10.1080/10286020.2012.669378.
The first biomimetic conversion from the aconitine-type C(19)-diterpenoid alkaloids to the corresponding alkaloids of lactone-type C(19)-diterpenoid alkaloid has been achieved. Chasmanine was used as starting material with Baeyer-Villiger oxidation as a key reaction. It was also observed that the oxygenated group at C-16 did not change the relative migration tendencies of C-13 and C-9 during the oxidation. Meantime, a novel D-ring fragmented compound was obtained during the course of the present investigation. The plausible mechanism of the formation of this compound was also proposed.
首次实现了从乌头碱型C(19)-二萜生物碱到相应内酯型C(19)-二萜生物碱的仿生转化。以查斯曼宁为起始原料，以拜耳-维利格氧化反应为关键反应。还观察到，在氧化过程中，C-16位的含氧基团并未改变C-13和C-9的相对迁移趋势。同时，在本研究过程中获得了一种新型的D环断裂化合物。还提出了该化合物形成的可能机制。
