212. Significance of the Geminal Dimethyl Group in the Odor Principle of Ambrox

Article abstract of DOI:10.1002/hlca.19850680726

The diastereoisomeric 18-nor- and 19-norambrox ((6α)- and (6β)-dodecahydro-3a,6,9a-trimethylnaphthol<2,1-b>furans resp.) as well as the corresponding 18,19-dinor-derivatives (dodecahydro-3a,9a-dimethylnaphtho<2,1-b>furans) have been synthesized and subjected to sensory evaluation.Threshold data and odor determination give an enlarged insight into the structure-activity relationship (SAR) in ambrox-type ambergris fragrances.As a general conclusion, the accumulation of axial CH3 groups in the tricyclic ethers 1-12 leads to the strongest receptor affinity.