Tetrahedron p. 10721 - 10736 (1996)
Update date:2022-08-05
Topics:
Brandstetter, Tilmann W.
De La Fuente, Carmen
Kim, Yong-ha
Johnson, Louise N.
Crook, Sarah
De Q. Lilley, Paul M.
Watkin, David J.
Tsitsanou, Katerina E.
Zographos, Spyros E.
Chrysina, Enangelia D.
Oikonomakos, Nikos G.
Fleet, George W.J.
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.
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