Issue 43, 2008

A diastereoselective route to 2,6-syn-disubstituted tetrahydropyrans: synthesis of the civet compound (+)-2-((2S,6S)-6-methyltetrahydro-2H-pyran-2-yl) acetic acid

Abstract

A diastereoselective synthesis of 2,6-syn-disubstituted tetrahydropyrans has been developed based on the ability of furanyletherchiral centres to epimerise readily under acidic conditions. This novel methodology was applied to the synthesis of (+)-2-((2S,6S)-6-methyltetrahydro-2H-pyran-2-yl) acetic acid, a component of the African civet cat’s glandular marking secretion.

Graphical abstract: A diastereoselective route to 2,6-syn-disubstituted tetrahydropyrans: synthesis of the civet compound (+)-2-((2S,6S)-6-methyltetrahydro-2H-pyran-2-yl) acetic acid

Article information

Article type
Communication
Submitted
17 Jun 2008
Accepted
01 Sep 2008
First published
30 Sep 2008

Chem. Commun., 2008, 5559-5561

A diastereoselective route to 2,6-syn-disubstituted tetrahydropyrans: synthesis of the civet compound (+)-2-((2S,6S)-6-methyltetrahydro-2H-pyran-2-yl) acetic acid

M. O’Brien, S. Cahill and L. A. Evans, Chem. Commun., 2008, 5559 DOI: 10.1039/B810231G

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