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 |
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Authors: | O'Brien Matthew Cahill Shane Evans Lyndsay A |
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Institution: | Whiffen Laboratory, University Chemical Laboratory, Cambridge University, Cambridge, UKCB2 1EW. mo263@cam.ac.uk |
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Abstract: | A diastereoselective synthesis of 2,6-syn-disubstituted tetrahydropyrans has been developed based on the ability of furanyl-ether chiral 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. |
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