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.
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.
O'Brien
Matthew
M
Whiffen Laboratory, University Chemical Laboratory, Cambridge University, Cambridge, UKCB2 1EW. mo263@cam.ac.uk
Cahill
Shane
S
Evans
Lyndsay A
LA
D000085:Acetates / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C534257:2-((2S,6S)-6-methyltetrahydro-2H-pyran-2-yl) acetic acid; D000085:Acetates; D011714:Pyrans