Abstract
[reaction: see text] A concise enantioselective preparation of oxazolidinylpiperidine 4, a key intermediate in the synthesis of glycosidase inhibitors such as 1-deoxymannojirimycin or 1-deoxygalactostatin, has been developed. Sharpless catalytic asymmetric epoxidation of (E)-2,4-pentadienol followed by treatment with allyl isocyanate afforded epoxy carbamate 8. Regioselective intramolecular ring opening promoted by sodium bis(trimethylsilyl)amide and ring-closing metathesis provided the bicyclic intermediate 4 in high enantiomeric purity. The four-step sequence takes place in 51% overall yield.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
1-Deoxynojirimycin / chemical synthesis
-
Aza Compounds / chemical synthesis*
-
Aza Compounds / pharmacology
-
Deoxy Sugars / chemical synthesis*
-
Deoxy Sugars / pharmacology
-
Enzyme Inhibitors / chemical synthesis*
-
Galactosamine / analogs & derivatives
-
Galactosamine / chemical synthesis
-
Glycoside Hydrolases / antagonists & inhibitors*
-
Molecular Structure
-
Piperidines / chemical synthesis
-
Piperidines / pharmacology
-
Stereoisomerism
Substances
-
Aza Compounds
-
Deoxy Sugars
-
Enzyme Inhibitors
-
Piperidines
-
5-amino-5-deoxygalactopyranose
-
1-Deoxynojirimycin
-
Galactosamine
-
Glycoside Hydrolases