A de novo synthesis of 2,6-dideoxy-C-aryl glycosides based on ring closing metathesis and diastereoselective epoxide cleavage/anomerization reactions.
[formula: see text] This paper describes a synthesis of enantiomerically pure 2,6-dideoxy-C-aryl glycosides, starting from non-carbohydrate precursors. The synthesis starts from homoallylic alcohols (obtained in enantiomerically pure form by enzymatic resolution), which are elaborated to dihydropyrans using ring closing metathesis as the key step. Epoxidation and epoxide cleavage complete the synthesis. The stereochemical outcome of the sequence depends on the conditions of the epoxide cleavage reaction.
Schmidt
B
B
Universität Dortmund, Fachbereich Chemie, Organische Chemie I, Germany. bschmidt@citrin.chemie.uni-dortmund.de
D000438:Alcohols / Q000737:chemistry; D016956:Burkholderia cepacia / Q000201:enzymology; D003837:Deoxy Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008049:Lipase; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D000438:Alcohols; D003837:Deoxy Sugars; D006027:Glycosides; D007202:Indicators and Reagents; D008049:Lipase