Department of Chemical and Biological Engineering/Organic Chemistry, Chalmers University of Technology, SE-412 96 Gothenburg, Sweden.
Org Lett. 2012 Dec 21;14(24):6274-7. doi: 10.1021/ol303036j. Epub 2012 Dec 10.
The first total synthesis of the mitotic spindle poison nostodione A is described. The inherent oxidative sensitivity of indoles is utilized for a late introduction of a second carbonyl to the cyclopent[b]indole-2-one system. The tricyclic system is prepared from indole-3-acetic acid and O-silylated 4-ethynylphenol, using a stereoselective intramolecular reductive Heck cyclization as the key transformation.
本文描述了有丝分裂纺锤体毒物诺多酮 A 的首次全合成。吲哚固有氧化敏感性用于后期将第二个羰基引入到环戊[b]吲哚-2-酮系统中。三环系统是由吲哚-3-乙酸和 O-硅基化的 4-乙炔基苯酚制备的，使用立体选择性的分子内还原 Heck 环化作为关键转化。
