title: Selective synthesis of hydroxy analogues of valinomycin using dioxiranes.
abstract: A 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.
authors: Dipartimento Chimica, Università di Bari A. Moro, v. Amendola 173, 70126 Bari, Italy. annese@chimica.uniba.it
authors: Cosimo
authors: C
authors: Annese
authors: Immacolata
authors: I
authors: Fanizza
authors: Cosima D
authors: CD
authors: Calvano
authors: Lucia
authors: L
authors: D'Accolti
authors: Caterina
authors: C
authors: Fusco
authors: Ruggero
authors: R
authors: Curci
authors: Paul G
authors: PG
authors: Williard
mesh_terms: D004852:Epoxy Compounds / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure; D014634:Valinomycin / Q000031:analogs & derivatives*
chemical_list: D004852:Epoxy Compounds; C061799:dioxirane; D014634:Valinomycin