The Synthesis and the Absolute Configurations of Lilac Alcohols, New Naturally Occurring Odorous Ingredients of Lilac Flower

The conversion of racemic linalyl acetate to racemic lilac alcohols has been completed in 5 steps and four diastereoisomers of β,5-dimethyl-5-vinyl-2-tetrahydrofuranethanol were obtained. d-Lilac alcohols were also synthesized from d-linalyl acetate and confirmed to be identical with natural ones. T...

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Bibliographic Details
Published inBulletin of the Chemical Society of Japan Vol. 46; no. 10; pp. 3183 - 3187
Main Authors Wakayama, Seiji, Namba, Satoshi, Hosoi, Kazuo, Ohno, Masaji
Format Journal Article
LanguageEnglish
Published The Chemical Society of Japan 01.10.1973
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Summary:The conversion of racemic linalyl acetate to racemic lilac alcohols has been completed in 5 steps and four diastereoisomers of β,5-dimethyl-5-vinyl-2-tetrahydrofuranethanol were obtained. d-Lilac alcohols were also synthesized from d-linalyl acetate and confirmed to be identical with natural ones. The absolute configurations of lilac alcohol-a, -b, -c, and -d were respectively shown to be (βS, 2S, 5S), (βR, 2S, 5S), (βR, 2R, 5S), and (βS, 2R, 5S) by the chemical and physical evidences.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.46.3183