Please use this identifier to cite or link to this item: http://hdl.handle.net/10553/47062
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
Pérez, Ricardo
Rico, Milagros 
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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