Synthesis of the Reported Structure of Pogostol and a Total Synthesis of (±)-Kessane without the Use of Protecting Groups

A short racemic synthesis of kessane from 4-hydroxy-4-methyl-2-cyclohexenone is described using a route that also resulted in the synthesis
of the reported structure of pogostol. The key step involves an Fe(III)-mediated tandem radical ring-expansion/cyclization of the cyclopropylsilyl
ether 9. No protecting groups are used in the entire sequence. Comparison of the NMR data of synthetic pogostol to that in the literature
indicates that the structure originally proposed is incorrect.