Hanson Paul R, Jayasinghe Susanthi, Maitra Soma, Markley Jana L
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr., 2010 Malott Hall, Lawrence, KS, 66045-7572, USA,
Top Curr Chem. 2015;361:253-71. doi: 10.1007/128_2014_572.
Recent advances in phosphate tether-mediated natural product synthesis are reviewed. Synthetic approaches toward dolabelide C, (-)-salicylihalimide A, (-)-tetrahydrolipstatin, and (+)-strictifolione are included. In addition, current efforts in method development are briefly reviewed, including a detailed study on the effect of stereochemical complexity on the phosphate-mediated, diastereoselective ring-closing metathesis reaction and recent advances in multi-reaction, one-pot sequential processes mediated by the phosphate tether. Overall, this review seeks to highlight the utility of phosphate triesters to serve as multifunctional tethers with protecting group and latent leaving group characteristics and the ability to orchestrate multiple, orthogonal reaction pathways to allow for the facile synthesis of complex, bioactive small molecules and their analogs.
本文综述了磷酸酯连接介导的天然产物合成的最新进展。其中包括多来肽C、(-)-水杨酰卤亚胺A、(-)-四氢利普他汀和(+)-硬叶内酯的合成方法。此外,还简要回顾了当前在方法开发方面的努力,包括对立体化学复杂性对磷酸酯介导的非对映选择性闭环复分解反应的影响的详细研究,以及磷酸酯连接介导的多反应一锅连续过程的最新进展。总体而言,本综述旨在突出磷酸三酯作为具有保护基团和潜在离去基团特性的多功能连接体的效用,以及协调多个正交反应途径以实现复杂生物活性小分子及其类似物的简便合成的能力。