Synthesis of the reported structure of pogostol and a total synthesis of (±)-kessane without the use of protecting groups

Kevin I. Booker-Milburn*, Helen Jenkins, Jonathan P H Charmant, Peter Mohr

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

25 Citations (Scopus)

Abstract

(Matrix presented) 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.

Translated title of the contributionSynthesis of the Reported Structure of Pogostol and a Total Synthesis of (±)-Kessane without the Use of Protecting Groups
Original languageEnglish
Pages (from-to)3309-3312
Number of pages4
JournalOrganic Letters
Volume5
Issue number18
DOIs
Publication statusPublished - 4 Sep 2003

Bibliographical note

Publisher: American Chemical Society

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