The State Key Laboratory and Institute of Elemento-organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University , Tianjin 300071, China.
Org Lett. 2018 Feb 2;20(3):668-671. doi: 10.1021/acs.orglett.7b03807. Epub 2018 Jan 24.
A redox-neutral α-C-H oxygenation of commercially available pyrrolidin-3-ol with a monoprotected p-quinone generated an N-aryliminium ion intermediate, which reacted in situ with boronic acid nucleophiles to produce a series of cis-2-substituted pyrrolidin-3-ols. With this strategy, 8-epi-(-)-lentiginosine was synthesized from (3R,4R)-pyrrolidine-3,4-diol in three steps.
一种商品化的吡咯烷-3-醇在单保护的对醌作用下发生α-C-H 的氧化还原中性反应,生成 N-芳基亚铵离子中间体,该中间体与硼酸亲核试剂就地反应,生成一系列顺式-2-取代的吡咯烷-3-醇。利用该策略,从(3R,4R)-吡咯烷-3,4-二醇出发,经过三步反应合成了 8-表-(-)-莱替丁醇。