Glucofuranose analogues of hydantocidin

Journal article

Epimeric spirohydantoins of glucofuranose, analogues of hydantocidin, are readily prepared from glucoheptonolactone. No rearrangement of spirohydantoins of glucofuranose to pyranose isomers was observed; a novel rearrangement was observed of a glucofuranose spirohydantoin to an isomeric oxazolidinone, (3aR,4'R,5S,6S,6aR)-5-(2',2'-dimethyl-1',3'-dioxolane-4'-yl)-6-hydroxy -3a-N-phenylcarboxamido-tetrahydrofuro[2.3-d]-1,2-oxazolidine-2-one, the structure of which was established by X-ray crystallographic analysis. The X-ray crystal structure of (1'R,2R,3R,4R,5R)-6,8-diaza-3,4-dihydroxy-2-(1',2'-dihydroxyethyl)-1-o xa-8-N-phenyl spiro[4.4]nonane-7,9-dione is reported.

Authors: Brandstetter, T; delaFuente, C; Kim, Y; Johnson, L; Crook, S

• Publication status: Published
• Journal: TETRAHEDRON
• Volume: 52
• Issue: 32
• Pages: 10721-10736
• Publication date: 1996-08-05
• DOI: 10.1016/0040-4020(96)00595-9
• ISSN: 0040-4020
• Language: English