A ring-closing metathesis strategy to phosphonosugars.
[reaction: see text]. Syntheses of cyclic phosphonate (phostone) analogues of carbohydrates containing a phosphorus atom at the anomeric position are described. The ring-closing metathesis reaction of mixed allylic phenyl esters of allylphosphonic acid 2 and 22 generates the six-membered allylic phosphonates 3 and 23 in excellent yields. Introduction of the polyhydroxy functionality in these cyclic phosphonates provides facile entry into an array of phostone sugar analogues.
Stoianova
D S
DS
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA.
Hanson
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PR
D002241:Carbohydrates / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D003500:Cyclization; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis*; D006601:Hexoses / Q000138:chemical synthesis; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis*; D017976:Phosphorus Acids / Q000138:chemical synthesis*
D002241:Carbohydrates; D006573:Heterocyclic Compounds, 1-Ring; D006601:Hexoses; D063065:Organophosphonates; D017976:Phosphorus Acids