Department of Applied Biological Sciences, Graduate School of Life and Environmental Sciences, Osaka Prefecture University, 1-1 Gakuencho, Nakaku, Sakai, Osaka 599-8531, Japan.
J Org Chem. 2021 Dec 17;86(24):17727-17737. doi: 10.1021/acs.joc.1c02026. Epub 2021 Dec 6.
A new method to synthesize γ-carboline derivatives has been developed starting from 3,5-dibromo-4-pyridinamine by monoarylation using the Suzuki-Miyaura cross-coupling reaction followed by the base-mediated ring closure to pyrrole formation. Synthesis of a series of γ-carboline derivations from the 4-brominated γ-carboline has been achieved by employing various coupling reactions and N-alkylations. This method has been applied for the synthesis of the antimalarial and anticancer natural product isocryptolepine. The photophysical properties of novel γ-carboline derivations are also reported.
已开发出一种从 3,5-二溴-4-吡啶胺出发，通过 Suzuki-Miyaura 交叉偶联反应进行单芳基化，然后进行碱介导的闭环形成吡咯，从而合成 γ-咔啉衍生物的新方法。通过各种偶联反应和 N-烷基化反应，从 4-溴代 γ-咔啉合成了一系列 γ-咔啉衍生物。该方法已应用于抗疟和抗癌天然产物异隐丹参酮的合成。还报道了新型 γ-咔啉衍生物的光物理性质。
