Selective Synthesis of Hydroxy Analogues of Valinomycin using Dioxiranes
2011; American Chemical Society; Volume: 13; Issue: 19 Linguagem: Inglês
10.1021/ol201971v
ISSN1523-7060
AutoresCosimo Annese, Immacolata Fanizza, Cosima Damiana Calvano, Lucia D’Accolti, Caterina Fusco, Ruggero Curci, Paul G. Williard,
Tópico(s)Synthesis and Biological Evaluation
ResumoA synthesis of representative monohydroxy derivatives of valinomycin (VLM) was achieved under mild conditions by direct hydroxylation at the side chains of the macrocyclic substrate using dioxiranes. Results demonstrate that the powerful methyl(trifluoromethyl)dioxirane 1b should be the reagent of choice to carry out these key transformations. Thus, a mixture of compounds derived from the direct dioxirane attack at the β-(CH(3))(2)C-H alkyl chain of one Hyi residue (compound 3a) or of one Val moiety (compounds 3b and 3c) could be obtained. Following convenient mixture separation, each of the new oxyfunctionalized macrocycles became completely characterized.
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