Synthèses stéréospécifiques et étude organoleptique comparée de onze triméthyl‐2,2,3‐exo‐norbornyl‐5‐exo‐cyclohexanols racémiques

Abstract

The stereospecific syntheses of the eleven racemic 2,2, exo‐3‐trimethyl‐exo‐5‐norbornyl‐cyclohexanols related to the formula VI have been achieved. Moreover, the fragrant properties of these isomeric and stereomeric cyclohexanols have been carefully estimated by a team of four well‐experienced perfumers. In good agreement with our earlier observations [1 ab], it was concluded that the axial 3‐(2,2, exo‐3‐trimethyl‐exo‐5‐norbornyl)‐cyclohexanols, threo (XXIV) and erythro (XXIX), are the only isomers which display a very powerful and genuine sandalwood odour. The other cyclohexanols were found to be about 20–100 times less fragrant (4 compounds), or practically odourless (5 compounds).