Molecules 2011, 16(7), 5362-5373; doi:10.3390/molecules16075362
Article

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

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Received: 2 June 2011; in revised form: 20 June 2011 / Accepted: 21 June 2011 / Published: 27 June 2011
(This article belongs to the Section Organic Synthesis)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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.
Keywords: ruthenium tetroxide; squalene; poly-THF; tetrahydrofuran; tetrahydropyran; rearrangement-ring expansion
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MDPI and ACS Style

Piccialli, V.; Zaccaria, S.; Centore, R.; Tuzi, A.; Borbone, N.; Oliviero, G. 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. Molecules 2011, 16, 5362-5373.

AMA Style

Piccialli V, Zaccaria S, Centore R, Tuzi A, Borbone N, Oliviero G. 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. Molecules. 2011; 16(7):5362-5373.

Chicago/Turabian Style

Piccialli, Vincenzo; Zaccaria, Sabrina; Centore, Roberto; Tuzi, Angela; Borbone, Nicola; Oliviero, Giorgia. 2011. "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." Molecules 16, no. 7: 5362-5373.

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