Highly stereocontrolled and regiocontrolled syntheses of polyoxygenated [2.2.2]oxabicyclic synthons
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- 作者：Rachel D. Slack ; Maxime A. Siegler ; Gary H. Posner
- 关键词：2-Pyrones ; Stereocontrol ; Regiocontrol ; Inverse electron demand Diels&ndash ; Alder reaction ; Carba-sugars
- 刊名：Tetrahedron Letters
- 出版年：2013
- 出版时间：13 November, 2013
- 年：2013
- 卷：54
- 期：46
- 页码：6267-6270
- 全文大小：799 K
文摘
Highly oxygenated cyclohexanes (known as cyclitols or carba-sugars) were synthesized regiospecifically and stereoselectively via a key inverse electron demand Diels-Alder cycloaddition of electron poor 2-pyrones with electron rich tert-butyldimethylsilyl vinyl ether. The resulting [2.2.2]oxabicyclic lactones proved to be versatile synthons; syn-dihydroxylations were achieved with very high stereocontrol, with up to five stereocenters being produced from commercially available or easily prepared planar starting materials.