Cedrón Juan C, Estévez-Braun Ana, Ravelo Angel G, Gutiérrez David, Flores Ninoska, Bucio María A, Pérez-Hernández Nury, Joseph-Nathan Pedro
Instituto Universitario de Bio-Organica "Antonio Gonzalez", Universidad de La Laguna, Av. Astrofísico Francisco Sanchez 2, 38206 La Laguna-Tenerife, Spain.
Org Lett. 2009 Apr 2;11(7):1491-4. doi: 10.1021/ol900065x.
An unexpected rearrangement of haemanthamine-type alkaloids in the presence of halogenating agents has been found. Rearranged compounds present the 5,11-methanomorphantridine framework characteristic of montanine-type alkaloids. These compounds are difficult to obtain because of their scarcity in natural sources and because the synthetic approaches developed so far require numerous steps. Vibrational circular dichroism (VCD) spectroscopy was used to determine the absolute configuration of one of the rearranged compounds. Several rearranged alkaloids showed antimalarial activity.
已发现血根碱型生物碱在卤化剂存在下会发生意外重排。重排后的化合物呈现出山地明型生物碱特有的5,11-甲桥吗啡烷啶骨架。由于这些化合物在天然来源中稀缺，且迄今为止开发的合成方法需要多个步骤，因此难以获得。振动圆二色性（VCD）光谱用于确定其中一种重排化合物的绝对构型。几种重排生物碱显示出抗疟活性。
