Nitro-polyols via Pyridine Promoted C═C Cleavage of 2-Nitroglycals. Application to the Synthesis of (−)-Hyacinthacine A1

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• 作者：Shengbiao Tang ; De-Cai Xiong ; Shende Jiang ; Xin-Shan Ye
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：February 5, 2016
• 年：2016
• 卷：18
• 期：3
• 页码：568-571
• 全文大小：371K
• ISSN：1523-7052

文摘

A mild and convenient transformation for the synthesis of nitro-polyols is described. The nitro-polyol derivatives were prepared either from 2-nitroglycals via a pyridine-promoted scission of the carbon–carbon double bond or from glycals via a sequential nitration–scission procedure. The generated nitro-polyols could undergo a stereoselective Michael addition reaction. The utility of the addition products was exemplified by the concise synthesis of (?)-hyacinthacine A1 and 7a-epi-(?)-hyacinthacine A1.