An In-Depth Study on Ring-Closing Metathesis of Carbohydrate-Derived α-Alkoxyacrylates: Efficient Syntheses of DAH, KDO, and 2-Deoxy-β-KDO
作者:Koen F. W. Hekking、Marcel A. H. Moelands、Floris L. van Delft、Floris P. J. T. Rutjes
DOI:10.1021/jo060913x
日期:2006.8.1
Novel, efficient synthetic pathways to DAH, KDO, and 2-deoxy-β-KDO are described. Ring-closing metathesis (RCM) of highly functionalized α-alkoxyacrylate fragments resulted in a series of synthetically versatile oxygen heterocyclic intermediates. Further functionalization of the resulting enol ether double bond and subsequent deprotection provided the natural products in high overall yields, starting
描述了通往DAH,KDO和2-deoxy-β-KDO的新颖,有效的合成途径。高度官能化的α-烷氧基丙烯酸酯片段的闭环复分解(RCM)导致了一系列合成上通用的氧杂环中间体。从可商购的被保护的糖开始,所得烯醇醚双键的进一步官能化和随后的脱保护以高的总收率提供了天然产物。