Simple Designs for the Construction of Complex Trans-Fused Polyether Toxin Frameworks. A Convergent Strategy Based on Hydroxy Ketone Cyclization of C-Linked Oxacycles |
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Authors: | Alvarez Eleuterio Pérez Ricardo Rico Milagros Rodríguez Rosa M Martín Julio D |
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Institution: | Centro de Productos Naturales Orgánicos Antonio González, Universidad de La Laguna-CSIC, Carretera de la Esperanza, 2, 38206 La Laguna, Tenerife, Spain. |
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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 |
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