Laboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, 15771 Athens, Greece.
Molecules. 2020 Dec 15;25(24):5939. doi: 10.3390/molecules25245939.
The chiral N1-Cbz, N2- derivative of the piperazic acid monomer is a valuable building block in the total synthesis of natural products, comprising this nonproteinogenic amino acid. In that context, we wish to report an improved synthetic protocol for the synthesis of both (3)- and (3)-piperazic acids bearing the carboxybenzyl protecting group (Cbz) selectively at the N1 position. Our method builds on previously reported protocols, circumventing their potential shortcomings, and optimizing the ultimate selective deprotection at the N2 position, thus, offering an efficient and reproducible pathway to suitably modified piperazates in high optical purity.
手性 N1-Cbz、N2-取代哌嗪酸单体是全合成天然产物中非常有价值的构建模块，包含这种非蛋白氨基酸。在这种情况下，我们希望报告一种改进的合成方案，用于选择性地在 N1 位置保护羧基苄基（Cbz）的（3）-和（3）-哌嗪酸的合成。我们的方法建立在以前报道的方案的基础上，避免了它们的潜在缺点，并优化了最终在 N2 位置的选择性脱保护，从而提供了一种高效且可重复的途径，以获得高光学纯度的合适修饰的哌嗪酸盐。
