Huang Junfeng, Bergmeier Stephen C
Department of Chemistry & Biochemistry, Ohio University, Athens, Ohio, 45701, USA.
Tetrahedron. 2008 Jun 30;64(27):6434-6439. doi: 10.1016/j.tet.2008.04.073.
A diastereoselective approach to 3,7,8-trisubstituted cis-decahydroquinolines is described. This ring system forms the core of rings B and E of the norditerpenoid alkaloid methyllycaconitine. This approach starts with a known disubsituted cyclohexene. The remaining carbons are attached via a Knoevenagel condensation followed by an intramolecular lactam formation. The stereochemistry of the substituents is controlled by the cis-substitution of the starting cyclohexene ring.
描述了一种对3,7,8-三取代顺式十氢喹啉的非对映选择性合成方法。该环系构成了去甲二萜生物碱甲基lycaconitine中B环和E环的核心。该方法从一种已知的二取代环己烯开始。其余的碳原子通过Knoevenagel缩合反应连接，随后进行分子内酰胺形成反应。取代基的立体化学由起始环己烯环的顺式取代控制。
