Graduate School of Bioagricultural Sciences, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8601, Japan.
J Org Chem. 2020 Jun 5;85(11):7534-7542. doi: 10.1021/acs.joc.0c00643. Epub 2020 May 22.
Chartelline C, a marine alkaloid, possesses a unique core scaffold including indolenine β-lactam and imidazole moieties linked by an unsaturated 10-membered ring. A new synthetic approach for the construction of the indolenine β-lactam was planned, based on the inherent reactivity of chartelline A with NaOMe, triggered by bromination of bromoenamide, and proceeding through an -acyl imine. However, the -acyl imine intermediate was not observed. Instead, the corresponding bromoindolenine was obtained, which led to the desired indolenine β-lactam in 92% yield.
Chartelline C 是一种海洋生物碱，具有独特的核心骨架，包括由不饱和 10 元环连接的吲哚啉 β-内酰胺和咪唑部分。计划基于 Chartelline A 与 NaOMe 的固有反应性，通过溴代溴烯酰胺引发，通过 -酰亚胺进行，设计了一种构建吲哚啉 β-内酰胺的新合成方法。然而，未观察到 -酰亚胺中间体。相反，得到了相应的溴代吲哚啉，以 92%的收率得到了所需的吲哚啉 β-内酰胺。
