title: Isolation of a bis-iodurated tetra-THF as a trace product from the oxidation of squalene with RuO₄ and its double ring expansion to a novel bis-THF-bis-THP compound.
abstract: A novel bis-iodurated polyether compound, based on an unprecedented tetra-THF backbone, has been isolated as a trace by-product of the oxidation of squalene with the catalytic system RuO₂(cat.)/NaIO₄. The double erythro configuration of the central portion of the molecule furnishes the first indirect support of the previously postulated pathway operating in the oxidative pentacyclization of the isoprenoid substrate. A bidirectional double oxidative bis-cyclization is invoked to explain the formation of this compound. The isolated substance was successfully subjected to a double rearrangement-ring expansion to give a novel bis-THF-bis-THP compound.
authors.affiliation: Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli "Federico II", Via Cynthia 4, 80126 Napoli, Italy. vinpicci@unina.it
authors.forename: Vincenzo
authors.initials: V
authors.lastname: Piccialli
authors.forename: Sabrina
authors.initials: S
authors.lastname: Zaccaria
authors.forename: Roberto
authors.initials: R
authors.lastname: Centore
authors.forename: Angela
authors.initials: A
authors.lastname: Tuzi
authors.forename: Nicola
authors.initials: N
authors.lastname: Borbone
authors.forename: Giorgia
authors.initials: G
authors.lastname: Oliviero
mesh_terms: D018360:Crystallography, X-Ray; D005663:Furans / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D017975:Ruthenium Compounds / Q000737:chemistry*; D013185:Squalene / Q000737:chemistry*
chemical_list: D005663:Furans; D017975:Ruthenium Compounds; C018674:tetrahydrofuran; D013185:Squalene