Department of Chemistry, Zhejiang University, Hangzhou 310027, China.
Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
Mar Drugs. 2023 Jun 25;21(7):373. doi: 10.3390/md21070373.
The concise and highly convergent synthesis of the isodityrosine unit of seongsanamide A-D and its derivatives bearing a diaryl ether moiety is described. In this work, the synthetic strategy features palladium-catalyzed C(sp)-H functionalization and a Cu/ligand-catalyzed coupling reaction. We report a practical protocol for the palladium-catalyzed mono-arylation of β-methyl C(sp)-H of an alanine derivative bearing a 2-thiomethylaniline auxiliary. The reaction is compatible with a variety of functional groups, providing practical access to numerous β-aryl-α-amino acids; these acids can be converted into various tyrosine and dihydroxyphenylalanine (DOPA) derivatives. Then, a CuI/-dimethylglycine-catalyzed arylation of the already synthesized DOPA derivatives with aryl iodides is described for the synthesis of isodityrosine derivatives.
本文描述了 seongsanamide A-D 的异二酪氨酸单元及其带有二芳基醚部分的衍生物的简洁、高度聚集的合成。在这项工作中，合成策略的特点是钯催化的 C(sp)-H 功能化和 Cu/配体催化的偶联反应。我们报告了一种实用的方案，用于钯催化带有 2-硫甲基苯胺辅助基的β-甲基 C(sp)-H 的单芳基化反应。该反应与各种官能团兼容，为许多β-芳基-α-氨基酸提供了实际途径;这些酸可以转化为各种酪氨酸和二羟基苯丙氨酸(DOPA)衍生物。然后，描述了已经合成的 DOPA 衍生物与芳基碘的 CuI/-二甲甘氨酸催化芳基化反应，用于合成异二酪氨酸衍生物。
