Abstract
The title compound, C22H34O6, is one of the products obtained by oxidation of squalene with the catalytic system RuO4(cat.)/NaIO4. It crystallizes in the P-1 space group, with four crystallographically independent mol-ecules related by a pseudo-C2 symmetry axis. The structural analysis also shows that the title compound is isomeric with two products previously reported in the literature and that are obtained by the same reaction procedure. In particular, out of the seven chiral C atoms present in the mol-ecule, the title compound shows the opposite configuration at, respectively, four and two chiral centres with respect to the isomeric compounds.
Highlights
The title compound, C22H34O6, is one of the products obtained by oxidation of squalene with the catalytic system RuO4(cat.)/NaIO4
The structural analysis shows that the title compound is isomeric with two products previously reported in the literature and that are obtained by the same reaction procedure
Our group has long been involved in the synthesis of new biologically active heterocyclic compounds, including purine nucleoside analogues (D’Errico et al, 2012a,b; Oliviero et al, 2008, 2010a,b), cyclic ethers (Piccialli et al, 2007, 2013), triazoles (Iovine et al, 2014) and spiroketal compounds (Piccialli et al, 2009; Piccialli, 2014)
Summary
The search for new lead compounds is a major goal in drug discovery and chemistry of materials (Teta et al, 2013). We have recently reported the synthesis of structurally new spiroketal compounds through ruthenium and chromium chemistry (Piccialli et al, 2009). The stereoselective polycyclization of squalene with catalytic amounts of RuO4 (Fig. 1) (Bifulco et al, 2003) allows pentaTHF 1 to be obtained in a straightforward way and high yields (50% for five consecutive cyclization steps; 87% per cyclization step) through a unique oxidative cascade process. In this way, multi-gram amounts of this substance can be obtained from a cheap starting material. X-ray diffraction experiment was undertaken in order to assess the differences in the stereochemistry with respect to the previously synthesized compounds and the possible mechanistic implications related to the concomitant formation of such stereoisomers in the same reaction
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