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Synthesis 1999; 1999(4): 695-703
DOI: 10.1055/s-1999-3444
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Design and Synthesis of Violet Odorants with Bicyclo[6.4.0]dodecene and Bicyclo[5.4.0]undecene Skeletons

Philip Kraft*
  • *Givaudan Roure Fragrance Research Ltd., CH-8600 Dübendorf, Switzerland; Fax +41(1)8 24 29 26; E-mail: philip.kraft@roche.com
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Publication Date:
31 December 1999 (online)

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The Diels-Alder reaction of 1,2-bis(methylene)cyclooctane (13), 4-methylenespiro[2,7]decane (29), 4-methylene-spiro[2.6]nonane (40) and 4-methylenespiro[2,7]dec-8-ene (46) with different α,β-unsaturated carbonyl compounds afforded various derivatives 16, 18, 20, 22, 24, 26, 32, 36, 38, 41, 42 and 47 of a molecular-modeled lead compound 9. These less flexible β-ionone-mimics with bicyclo[6.4]dodecene and bicyclo[5.4.0]undecene skeletons possess interesting fruity-woody-floral odor notes and provide insight into the structure-odor correlation of violet odorants. 5-(2-Methylcycloalk-1-en-1-yl)hex-3-en-2-ones (e. g. 35) were identified as byproducts of the Rh(I)-catalyzed reactions of the vinylcyclopropanes 29 and 40.

cycloadditions - ionones - molecular modeling - vinylcyclopropanes - Wilkinson's catalyst