Enantiospecific synthesis, separation and olfactory evaluation of all diastereomers of a homologue of the sandalwood odorant Polysantol |
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Authors: | Juan M Castro Manuel Nogueras Adolfo Sánchez |
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Institution: | Departamento de Química Inorgánica y Orgánica, Facultad de Ciencias Experimentales, Universidad de Jaén, 23071 Jaén, Spain |
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Abstract: | 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. |
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Keywords: | α-Campholenic aldehyde derivatives α-Pinene Enantiospecific synthesis Organoleptic evaluation Sandalwood Odorants |
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