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dc.contributorWichita State University. Department of Chemistryen_US
dc.contributor.authorOlabisi, Ayodele O.en_US
dc.contributor.authorMahindaratne, Mathew P. D.en_US
dc.contributor.authorWimalasena, Kandategeen_US
dc.identifierNS 39423en_US
dc.identifier.citationThe Journal of organic chemistry. 2005 Aug 19; 70(17): 6782-9.en_US
dc.descriptionClick on the DOI link below to access the article (may not be free).en_US
dc.description.abstractA convenient method to obtain unknown chiral C2- and C3-functionalized aldono-1,4-lactone derivatives starting from l-ascorbic acid, which would be valuable in the synthesis of derivatives of various pharmacologically active agents for structure-activity studies, is described. The practicality of this approach is demonstrated by the synthesis of a series of 5,6-O-isopropylidene-2-allyl-3-keto-l-galactono-gamma-lactone and 5,6-O-isopropylidene-3-allyl-2-keto-l-galactono-gamma-lactone derivatives using the thermal Claisen rearrangement of the corresponding 3-O- and 2-O-allyl derivatives of 5,6-O-isopropylidene-l-ascorbic acid, respectively, followed by stereospecific reduction to the corresponding alcohols. The synthetic steps are shown to be efficient, and enantiospecific, and they proceed with high yields.en_US
dc.description.sponsorshipNINDS NIH HHSen_US
dc.publisherAmerican Chemical Societyen_US
dc.relation.ispartofseriesThe Journal of organic chemistryen_US
dc.relation.ispartofseriesJ. Org. Chem.en_US
dc.subjectResearch Support, N.I.H., Extramuralen_US
dc.subject.meshAscorbic Acid/chemistryen_US
dc.subject.meshMagnetic Resonance Spectroscopyen_US
dc.subject.meshSugar Acids/chemistryen_US
dc.titleA convenient entry to C2- and C3-substituted gulono-gamma-lactone derivatives from L-ascorbic aciden_US
dc.coverage.spacialUnited Statesen_US
dc.description.versionpeer revieweden_US
dc.rights.holderCopyright © 2005 American Chemical Societyen_US

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