Stereoselective synthesis of 3-oxygenated-cis-dialkyl-2,5-substituted tetrahydrofurans from cyclohexadienediols |
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Authors: | Brovetto Margarita Seoane Gustavo |
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Institution: | Departamento de Química Orgánica, Facultad de Química, Universidad de la República, C.C. 1157, Montevideo, Uruguay. mbrovett@fq.edu.uy |
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Abstract: | The 3-oxygenated-cis-dialkyl-2,5-substituted tetrahydrofuran system, present in several natural products, was prepared with good selectivity by acidic cyclization of 5-alkene-1,2,4-triol derivatives. The starting alkenol was obtained in few steps from a chiral cis-diol resulting from microbial oxidation of bromobenzene. The study of the cyclization allowed the rationalization of all experimental results by assuming a complete ionization at the allylic position and a model close to the one proposed by Labelle for homoallylic induction in five-membered ring closures. |
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