Institut für Organische Chemie, Universität des Saarlandes, Campus C4.2, 66123, Saarbrücken, Germany.
Chemistry. 2021 Jan 13;27(3):949-953. doi: 10.1002/chem.202004650. Epub 2020 Dec 15.
Application of ester dienolates as nucleophiles in Matteson homologations allows for the stereoselective synthesis of highly substituted α,β-unsaturated δ-hydroxy carboxyl acids, structural motifs widespread found in polyketide natural products. The protocol is rather flexible and permits the introduction of substituents and functionalities also at those positions which are not accessible by the commonly used aldol reaction. Therefore, this ester dienolate Matteson approach is an interesting alternative to the "classical" polyketide syntheses.
酯烯醇盐作为亲核试剂在 Matteson 同系化反应中的应用允许立体选择性合成高度取代的α,β-不饱和δ-羟基羧酸,这些结构基序广泛存在于聚酮类天然产物中。该方案相当灵活,并允许在通常的醛醇反应无法到达的位置引入取代基和官能团。因此,这种酯烯醇盐 Matteson 方法是对“经典”聚酮合成的一个有趣的替代。