Abstract
From isophorone (1) and camphor (2) the spiro ethers 3–8 were prepared via the yne-diols 12–17 and the ene-diols 18–23. The attempted ring closure of 21 and 22 with KHSO4 furnished only the carbonyl compounds 24 and 25. Under these conditions 23 gave a mixture of the isomers 8a and 8b. Olfactive evaluation showed that the odour goes stepwise with increasing substitution at C-2 (3 4 5) or C-5′ (6 7 8) from harsh, camphoraceous to fruity and finally nutty, woody notes. These sensations are comparable with those of the dehydrotheaspiranes (type B) showing that the methyl groups in a position to the osmophoric oxygen atom are particularly important for the odour profile. The strongly hindered interaction of the ether atom of 8a with the receptor in comparison to the situation of the isomer 8b effects a great difference in both odour quality and quantity of these isomers.
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