Snyder Scott A, Tang Zhen-Yu, Gupta Ritu
Department of Chemistry, Columbia University, 3000 Broadway, New York, New York 10027, USA.
J Am Chem Soc. 2009 Apr 29;131(16):5744-5. doi: 10.1021/ja9014716.
The napyradiomycins are an intriguing family of halogenated natural products with activity against several tumor cell lines as well as some of the worst bacterial strains known to humanity, including methicillin-resistant Staphylococcus aureas and vancomycin-resistant strains of Enterococcus faecium. This communication delineates the first asymmetric total synthesis of (-)-napyradiomycin A1 by a strategy that features a two-step total synthesis of flaviolin, the first highly asymmetric halogenation of a simple alkene, and a Johnson-Claisen rearrangement that generates a quaternary carbon next to a glucal-like oxygen.
萘并放线菌素是一类有趣的卤代天然产物，对多种肿瘤细胞系以及一些人类已知的最具耐药性的细菌菌株具有活性，包括耐甲氧西林金黄色葡萄球菌和耐万古霉素屎肠球菌。本论文阐述了(-)-萘并放线菌素A1的首次不对称全合成，该合成策略的特点包括两步法全合成黄酮灵、简单烯烃的首次高度不对称卤化，以及在类葡糖醛酸氧邻位生成一个季碳的约翰逊-克莱森重排反应。
