An in-depth study on ring-closing metathesis of carbohydrate-derived alpha-alkoxyacrylates: efficient syntheses of DAH, KDO, and 2-deoxy-beta-KDO

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

doi:10.1021/jo060913x

An in-depth study on ring-closing metathesis of carbohydrate-derived alpha-alkoxyacrylates: efficient syntheses of DAH, KDO, and 2-deoxy-beta-KDO

J Org Chem. 2006 Aug 18;71(17):6444-50. doi: 10.1021/jo060913x.

Authors

Koen F W Hekking¹, Marcel A H Moelands, Floris L van Delft, Floris P J T Rutjes

Affiliation

¹ Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, NL-6525 ED Nijmegen, The Netherlands.

PMID: 16901129
DOI: 10.1021/jo060913x

Abstract

Novel, efficient synthetic pathways to DAH, KDO, and 2-deoxy-beta-KDO are described. Ring-closing metathesis (RCM) of highly functionalized alpha-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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acrylates / chemistry*
Alkylation
Carbohydrates / chemistry*
Catalysis
Isomerism
Molecular Structure
Oxygen / chemistry*
Sugar Acids / chemical synthesis*
Sugar Acids / chemistry
Sugar Phosphates / chemical synthesis*
Sugar Phosphates / chemistry

Substances

Acrylates
Carbohydrates
Sugar Acids
Sugar Phosphates
2-keto-3-deoxyoctonate
3-deoxy-D-arabino-heptulosonate-7-phosphate
acrylic acid
Oxygen