An In-Depth Study on Ring-Closing Metathesis of
Carbohydrate-Derived α-Alkoxyacrylates:  Efficient Syntheses of
DAH, KDO, and 2-Deoxy-β-KDO

F. W. Hekking, Koen; A. H. Moelands, Marcel; L. van Delft, Floris; P. J. T. Rutjes, Floris

doi:10.1021/jo060913x.s001

jo060913x_si_001.pdf (851.83 kB)

An In-Depth Study on Ring-Closing Metathesis of Carbohydrate-Derived α-Alkoxyacrylates: Efficient Syntheses of DAH, KDO, and 2-Deoxy-β-KDO

journal contribution

posted on 2006-08-18, 00:00 authored by Koen F. W. Hekking, Marcel A. H. Moelands, Floris L. van Delft, Floris P. J. T. Rutjes

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 from commercially available protected sugars.