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Efficient conversion of carbohydrates into 1-C-alditols: application to the synthesis of chiral gamma-substituted butenolides and bicyclic alkaloid analogues

AuthorsBoto, Alicia ; Hernández, Dácil ; Hernández, Rosendo
Issue Date13-Jun-2008
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 73(14): 5287-5297 (2008)
AbstractReadily available sugar derivatives were transformed in a few steps into valuable, more complex products. The tandem radical scission of carbohydrates-oxidation reaction gave acetoxy acetals, which were converted into a variety of chiral C-alditols in good global yields and excellent 1,2-trans stereoselectivity. The reaction was the key step in the synthesis of hydroxylated gamma-substituted butenolides and bicyclic alkaloid analogues.
Description11 pages, 2 figures, 2 tables, 7 schemes.-- PMID: 18549274 [PubMed].-- Printed version published Jul 18, 2008.-- Supporting information available: Preparation of substrate 22, including spectroscopic data of the synthetic intermediates and the final product. Procedures for the allylation and alkylation reactions, and spectroscopic data of phenyl ketones 20, 21, 27, butenolides 28-33 and 37-39, and cyclohexanones 46, 47, and 49. 1H and 13C NMR spectra for acetoxy acetal 24, allyl derivatives 18 and 19, phenyl ketones 20, 21, 26, and 27, butenolides 28-39, cyclohexanones 46-48 and 50-55, alkaloid analogues 56-61, and substrates 63-65 and 22.-- Available at: http://pubs.acs.org/doi/suppl/10.1021/jo800478a
Publisher version (URL)http://dx.doi.org/10.1021/jo800478a
Appears in Collections:(IPNA) Artículos
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