Jump to main content
Jump to site search

Issue 43, 2008
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Publication details

The article was received on 17 Jun 2008, accepted on 01 Sep 2008 and first published on 30 Sep 2008


Article type: Communication
DOI: 10.1039/B810231G
Chem. Commun., 2008, 5559-5561

  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements