Analogues of the Quararibea metabolite chiral enolic-gamma-lactone from (2S,3S)- and (2S,3R)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylic acids

dc.contributor.author	Chithra Gopinath
dc.contributor.author	Salini Thomas
dc.contributor.author	Mangalam S Nair
dc.contributor.author	Ibnusaud, I
dc.date.accessioned	2015-01-08T08:06:38Z
dc.date.available	2015-01-08T08:06:38Z
dc.date.issued	2006
dc.identifier.citation	Tetrahedron Letters 47(45):7957-7960;6 Nov 2006	en_US
dc.identifier.issn	0040-4039
dc.identifier.uri	http://ir.niist.res.in:8080/jspui/handle/123456789/1740
dc.description.abstract	Reaction of dialkyl (2S,3S)- or (2S,3R)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylates with POCl3 in pyridine followed by diazomethane resulted in the isolation of dialkyl 2S-4-methoxy-5-oxo-2,5-dihydro-2,3-furandicarboxylates, which are analogues of the Quararibea metabolite chiral enolic-gamma-lactone (3-hydroxy-4,5-(R)-dimethyl-2(5H)-furanone). An unusual alpha-hydroxylation of gamma-butyrolactone takes place involving POCl3 in pyridine. When the dehydration was facilitated with methanesulfonyl chloride in triethylamine, instead of POCl3, aromatic dialkyl 5-[(methylsulfonyl)oxy]-2,3-furandicarboxylates were obtained.	en_US
dc.language.iso	en	en_US
dc.publisher	Elsevier	en_US
dc.subject	Garcinia acid	en_US
dc.subject	hibiscus acid	en_US
dc.subject	chiral butenolide	en_US
dc.title	Analogues of the Quararibea metabolite chiral enolic-gamma-lactone from (2S,3S)- and (2S,3R)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylic acids	en_US
dc.type	Article	en_US