作者:Martina De Angelis、Ludovica Primitivo、Claudia Lucarini、Sonia Agostinelli、Carla Sappino、Alessandra Ricelli、Giuliana Righi
DOI:10.1016/j.carres.2020.108028
日期:2020.6
The first stereocontrolled total synthesis of iminosugar 1,4-dideoxy-1,4-imino-D-iditol is described. The key step in our approach was the double diastereoselection in the asymmetric dihydroxylation (AD) of suitable optically active olefin, the chiral vinyl azido alcohol 9. Performing the AD using the most common Cinchona alkaloids as ligands enabled us to identify the ligand of choice for the stereodivergent
描述了亚氨基糖1,4-二脱氧-1,4-亚氨基-D-ID-糖醇的第一个立体控制的全合成。我们方法的关键步骤是合适的旋光性烯烃手性乙烯基叠氮醇9的不对称二羟基化(AD)中的双非对映选择性。使用最常见的金鸡纳生物碱作为配体进行AD使我们能够确定用于选择的配体1,4-二脱氧-1,4-亚氨基-D-半乳糖醇和1,4-二脱氧-1,4-亚氨基-D-半乳糖醇的立体发散合成。这类天然和非天然的亚氨基糖因其针对病毒感染,糖尿病,癌症和肺结核的有前途的化学治疗性能而得到了深入研究。