Synthesis of Enantiopure 2-C-Glycosyl-3-nitrochromenes

详细信息    查看全文

• 作者：Raquel G. Soengas ; Humberto Rodr铆guez-Solla ; Artur M. S. Silva ; Ricardo Llavona ; Filipe A. Almeida Paz
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：December 20, 2013
• 年：2013
• 卷：78
• 期：24
• 页码：12831-12836
• 全文大小：325K
• 年卷期：v.78,no.24(December 20, 2013)
• ISSN：1520-6904

文摘

A novel methodology has been developed to obtain enantiopure 2-C-glycosyl-3-nitrochromenes. First, (Z)-1-bromo-1-nitroalkenes were prepared from the corresponding sugar aldehydes through a sodium iodide-catalyzed Henry reaction with bromonitromethane followed by elimination of the resulting 1-bromo-1-nitroalkan-2-ols. In the next step, reaction of the sugar-derived (Z)-1-bromo-1-nitroalkenes with o-hydroxybenzaldehydes afforded enantiopure (2S,3S,4S)-3-bromo-3,4-dihydro-4-hydroxy-3-nitro-2H-1-benzopyrans, which, upon SmI₂-promoted 尾-elimination, yielded chiral enantiopure 2-C-glycosyl-3-nitrochromenes.