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Closed Access item β-Fragmentation of primary alkoxyl radicals versus hydrogen abstraction: synthesis of polyols and α,ω-differently substituted cyclic ethers from carbohydrates

Authors:Boto, Alicia
Hernández, Dácil
Hernández, Rosendo
Suárez, Ernesto
Issue Date:28-May-2003
Publisher:American Chemical Society
Citation:Journal of Organic Chemistry 68(13): 5310-5319 (2003)
Abstract:The β-fragmentation of primary alkoxyl radicals, described in many cases as low-yielding and plagued by side reactions, can proceed in satisfactory yields using carbohydrate substrates. The only reaction that can compete significantly with the β-scission is the intramolecular hydrogen abstraction. The ratio of β-fragmentation to hydrogen abstraction can be varied according to the reaction conditions, the stereochemistry of the substituents (e.g., α- or β-anomeric substituents), and the protecting groups chosen. The carbohydrate substrates are easily prepared, and the mild reaction conditions are compatible with most functional groups. The β-scission reaction provides an expedient way toward shorter and less common sugar series and also toward α,ω-differently substituted cyclic ethers. These units are useful building blocks and are present in many natural products with interesting biological activity.
Description:10 pages, 2 figures, 2 tables, 7 schemes.-- PMID: 12816493 [PubMed].-- Printed version published Jun 27, 2003.
Publisher version (URL):http://dx.doi.org/10.1021/jo034442f
Appears in Collections:(IPNA) Artículos

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