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

The four stereoisomers of (5 E)-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...

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Bibliographic Details
Published in:Tetrahedron 2005-11, Vol.61 (47), p.11192-11203
Main Authors: Castro, Juan M., Linares-Palomino, Pablo J., Salido, Sofía, Altarejos, Joaquín, Nogueras, Manuel, Sánchez, Adolfo
Format: Article
Language:English
Subjects:
Enantiospecific synthesis
Odorants
Organoleptic evaluation
Sandalwood
α-Campholenic aldehyde derivatives
α-Pinene
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Summary:The four stereoisomers of (5 E)-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 (−)-(1 S)-camphanic chloride. The enantiomerically pure final products were evaluated organoleptically. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.09.023