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 rearrangementring expansion to give a novel bis-THF-bis-THP compound. © 2011 by the authors; licensee MDPI, Basel, Switzerland.