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

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

1
Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli "Federico II", Via Cynthia 4, 80126, Napoli, Italy
2
Dipartimento di Chimica ‘‘Paolo Corradini’’, Università degli Studi di Napoli ‘‘Federico II’’, Via Cinthia 4, 80126, Napoli, Italy
3
Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli "Federico II", Via D. Montesano 49, 80131, Napoli, Italy
*
Author to whom correspondence should be addressed.
Received: 2 June 2011 / Revised: 20 June 2011 / Accepted: 21 June 2011 / Published: 27 June 2011
(This article belongs to the Section Organic Synthesis)
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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 ruthenium tetroxide; squalene; poly-THF; tetrahydrofuran; tetrahydropyran; rearrangement-ring expansion
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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