Enantiospecific synthesis, separation and olfactory evaluation of all diastereomers of a homologue of the sandalwood odorant Polysantol

Article abstract of DOI:10.1016/j.tet.2005.09.023

The four stereoisomers of (5E)-4,4-dimethyl-6-(2′,2′,3′- trimethylcyclopent-3′-en-1′-yl)-hex-5-en-3-ol, a homologue of the valuable sandalwood-type odorant Polysantol, were enantiospecifically synthesized from (+)- and (-)-α-pinene, through (-)- and (+)-campholenic aldehyde, by aldol condensation with 3-pentanone, deconjugative α-methylation and reduction. The mixtures of epimeric alcohols obtained after reduction were separated by means of derivatization with (-)-(1S)-camphanic chloride. The enantiomerically pure final products were evaluated organoleptically.