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Stereocontrolled photocyclization of 1,2-diketones: application of a 1,3-acetyl group transfer methodology to carbohydrates

AuthorsHerrera, Antonio J. ; Rondón, María ; Suárez, Ernesto
Issue Date28-Mar-2008
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 73(9): 3384-3391 (2008)
AbstractPhotolysis of 1-glycosyl-2,3-butanodione derivatives using visible light is a mild and selective procedure for the synthesis of chiral 1-hydroxy-1-methyl-5-oxaspiro[3.5]nonan-2-one carbohydrate derivatives. The results strongly suggest that stereocontrol of the cyclization is dependent on conformational and stereoelectronic factors. Further oxidative opening of the 1-hydroxy-1-methyl-2-cyclobutanone moiety affords new C-ketoside derivatives either in C- and O-glycoside series. This tandem two-step process could be considered to be a stereocontrolled 1,3-transference of an acetyl group, and it can be applied either to pyranose and furanose models.
Description8 pages, 1 figure, 2 tables, 6 schemes.-- PMID: 18370422 [PubMed].-- Printed version published May 2, 2008.
Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo702663w
Publisher version (URL)http://dx.doi.org/10.1021/jo702663w
Appears in Collections:(IPNA) Artículos
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