Preparation of some deuterium labelled 9- and/or 10-oxygenated derivatives of geraniol, geranial, nerol, and neral

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Abstract
The preparation of various deuterium labelled 9- and/or 10-oxygenated derivatives of geraniol, geranial, nerol, and neral is described. Wittig reaction of the tetrahydropyranyl ethers of (E)- and (Z)-1,1-dideutero-6-(triphenylphosphonium)-3-methyl-2-hexen-1-ol iodides (23 and 24) with the tetrahydropyranyl ethers of hydroxyacetone and 1,3-dihydroxyacetone afforded, after deprotection, C-1 dideuterated 9-hydroxygeraniol, 9-hydroxynerol, 9,10-dihydroxygeraniol, and 9,10-dihydroxynerol of high isomeric purity. Selective oxidation of these products allowed for the preparation of the corresponding derivatives possessing an aldehyde functionality at C-9 or C-1 and C-9. Wittig reaction of 23 and 24 with pyruvaldèhyde dimethyl acetal followed by acidic hydrolysis afforded C-1 dideuterated 10-oxogeraniol and 10-oxonerol, oxidation of which yielded C-1 deuterated 10-oxogeranial and 10-oxoneral. Wittig reaction of (E)- and (Z)-1,1-dideutero-6-(triphenyl-phosphonium)-3-methyl-2-hexen-1-ol iodides (49 and 50) with 1,1,3,3-tetraethoxyacetone afforded C-1 dideuterated 9,9,10,10-tetraethoxygeraniol and 9,9.10,10-tetraethoxynerol, oxidation of which provided C-1 deuterated 9,9,10,10-tctraethoxygeranial and 9,9,10,10-tetraethoxyneral.

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