|Title:||Simple designs for the construction of complex trans-fused polyether toxin frameworks. A convergent strategy based on hydroxy ketone cyclization of C-linked oxacycles||Authors:||Alvarez, Eleuterio
Rodríguez, Rosa M.
Martín, Julio D.
|UNESCO Clasification:||2306 Química orgánica||Issue Date:||1996||Publisher:||0022-3263||Journal:||Journal of Organic Chemistry||Abstract:||A single, unified convergent strategy for the stereocontrolled synthesis of trans-fused polyethers was developed. It was demonstrated that the epimerization and reductive intramolecular coupling of hydroxy ketones in reactions with silane−Lewis acids (SI−LA) to generate ethers in C-linked oxacycles is affected by its conformational preference in a predictable manner. The obtained results make evident that the influence of hydrogen bonding between a hemiketal hydroxyl and a 1,3-diaxial C−O bond is regular and predictable and that convergent synthesis of trans-fused polyethers may confidently be conducted on driving ring closure to oxane rings under thermodynamic conditions||URI:||http://hdl.handle.net/10553/47062||ISSN:||0022-3263||DOI:||10.1021/jo950547+||Source:||Journal of Organic Chemistry [ISSN 0022-3263], v. 61, p. 3003-3016|
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