title: Synthesis of the reported structure of pogostol and a total aynthesis of (+/-)-kessane without the use of protecting groups.
abstract: [reaction: see text] 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.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK. k.booker-milburn@bristol.ac.uk
authors.forename: Kevin I
authors.initials: KI
authors.lastname: Booker-Milburn
authors.forename: Helen
authors.initials: H
authors.lastname: Jenkins
authors.forename: Jonathan P H
authors.initials: JP
authors.lastname: Charmant
authors.forename: Peter
authors.initials: P
authors.lastname: Mohr