Department of Chemistry, Korea University, Seoul 02841, Republic of Korea.
Org Lett. 2020 Jun 19;22(12):4653-4658. doi: 10.1021/acs.orglett.0c01428. Epub 2020 Jun 1.
We describe the asymmetric total syntheses of naphthylisoquinoline alkaloids. Atroposelective biaryl coupling reaction between naphthyl pinacol boronate and an aryl iodide, bearing ()-2-aminopropyl group at the -position using the existing central chirality as an atroposelectivity-controlling group, provided the desired biaryl product with high atroposelectivity, without the use of an external chiral source. From the resulting biaryl product, several naphthylisoquinoline alkaloids were prepared via the stereoselective formation of the isoquinoline framework with the appropriate oxidation state and stereochemistry.
我们描述了萘基异喹啉生物碱的不对称全合成。使用现有的中心手性作为手性控制基团，在萘基频哪醇硼酸酯和带有（）-2-氨基丙基的芳基碘化物之间进行非对映选择性联芳基偶联反应，无需使用外部手性源，即可高非对映选择性地得到所需的联芳基产物。从得到的联芳基产物出发，通过适当的氧化态和立体化学构建异喹啉骨架，制备了几种萘基异喹啉生物碱。
