Hocine Sofiane, Duchamp Edouard, Mishra Akash, Fourquez Jean-Marie, Hanessian Stephen
Department of Chemistry, Université de Montréal, Station Centre-Ville, C.P. 6128, Montreal, Quebec H3C 3J7, Canada.
Institut de Recherches Servier, 125 Chemin de Ronde, 78290 Croissy, France.
J Org Chem. 2023 Apr 7;88(7):4675-4686. doi: 10.1021/acs.joc.3c00169. Epub 2023 Mar 20.
We report the synthesis of two novel azaperhydroazulene tropane-hederacine chimeras and , which contain an 8-azabicyclo[3.2.1]octane ring and a 7-azabicyclo[4.1.1]octane ring, respectively. The synthesis of both chimeras was achieved by epoxide ring opening and was governed by the stereochemistry of the hydroxy-epoxide unit. Finally, a density functional theory study was conducted to explain the regioselectivity of the cyclization and the importance of the stereochemistry of the hydroxyl group.
我们报道了两种新型氮杂氢化薁托烷-常春藤皂苷元嵌合体 和 的合成，它们分别含有一个8-氮杂双环[3.2.1]辛烷环和一个7-氮杂双环[4.1.1]辛烷环。两种嵌合体的合成均通过环氧开环实现，并受羟基环氧单元的立体化学控制。最后，进行了密度泛函理论研究，以解释环化的区域选择性和羟基立体化学的重要性。
