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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 7
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Original Articles

New Straightforward Synthesis of β‐Damascenone and β‐Damascone Derivatives from β‐Ionone via Retro‐α‐ionol

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Pages 1077-1090 | Received 04 Aug 2006, Published online: 13 Oct 2010

References

  • Ohloff , G. 1994 . “ Violet odorants and rose ketones ” . In Scent and Fragrances 117 Berlin : Springer‐Verlag .
  • Williams , A. 2002 . Rose ketones: Celebrating 30 years of success . Perfumer Flavorist , 27 : 18 – 31 .
  • Ohloff , G. 1978 . “ Recent development in the field of naturally occuring aroma components ” . In Progress in the Chemistry of Organic Natural Products Edited by: Hertz , W. , Grisenbach , H. and Kirby , G. W. Vol. 35 , 431 New York : Springer‐Verlag .
  • Bedoukian , P. Z. 1982 . “ Violet fragrance compounds ” . In Fragrance Chemistry: The Science of the Sense of Smell Edited by: Theimer , E. T. New York : Academic Press .
  • Fehr , C. 1997 . “ Enantioselective protonation in fragrance synthesis ” . In Chirality in Industry II Edited by: Collins , A. N. , Sheldrake , G. N. and Crosby , J. 335 Chichester : Wiley .
  • Ohloff , G. 1978 . Importance of minor compounds in flavors and fragrances . Perfumer Flavorist , 3 ( 2 ) : 11 – 22 .
  • Buttery , R. G. , Teranishi , G. and Ling , L. C. 1988 . Identification of damascenone in tomato volatiles . Chem. Ind. (London) , : 238
  • Ohloff , G. and Uhde , G. 1970 . Über eine ungewöhnliche Cyclisationsreaktion bei der Umsetzung von (+)‐Epoxy‐α‐dihydrojonon mit Hydrazinhydrat . Helv. Chim. Acta , 53 : 531 – 541 .
  • Demole , E. , Enggist , P. , Saüberli , U. , Stoll , M. and Kovats , E. 1970 . Structure et synthèse de la damascénone (triméthyl‐2,6,6‐trans‐crotonoyl‐1‐cyclohexadiène‐1,3), constituant odorant de l'esssence de rose bulgare (Rosa damascena Mill.) . Helv. Chim. Acta , 53 : 541 – 551 .
  • Schreier , P. and Drawert , F. 1974 . Gaschromatographisch‐massenspektrometrische Untersuchung flüchtiger Inhaltsstofe des Weines, I: Unpolare Verbindungen des Weisnaromas . Z. Lebensm. Unters. Forsch. , 154 ( 5 ) : 273 – 278 .
  • Sefton , M. A. , Skouroumounis , G. K. , Massy‐Westropp , R. A. and Williams , P. J. 1989 . Nor‐isoprenoids in Vitis vinifera white wine grapes and the identification of a precursor of damascenone in these fruits . Aust. J. Chem. , 42 : 2071 – 2084 .
  • Demole , E. and Berthet , D. 1971 . Identification de la damascénone et de la β‐damascone dans le tabac . Burley. Helv. Chim. Acta , 54 : 681 – 682 .
  • Winter , M. and Enggist , P. 1971 . Recherches sur les arômes: Sur l'arôme de framboise, IV . Helv. Chim. Acta , 54 : 1891 – 1898 .
  • Renold , W. , Näf‐Müller , R. , Keller , U. , Willhalm , B. and Ohloff , G. 1974 . An investigation of the tea aroma, part I: New volatile black tea constituents . Helv. Chim. Acta , 57 : 1301 – 1308 .
  • Strating , J. and Eerde , P. V. 1973 . Staling of beer . J. Inst. Brew. (London) , 79 : 414 – 415 .
  • Maarse , H. and Visscher , C. A. 1996 . Volatile Compounds in Alcoholic Beverages—Qualitative and Quantitative Data Zeist : TNO‐CIVO Food Analysis Institute .
  • Kovats , E. , Demole , E. , Stoll , M. and Ohloff , G. 1970 . (Firmenich et Cie). Cycloaliphatic unsaturated ketones for use as perfumes . Ger. Offen. , 2 : 022 – 216 .
  • Schulte‐Elte , K. H. , Müller , B. and Ohloff , G. 1973 . Synthetische Übergänge von der Jonon‐ in die Damasconreihe . Helv. Chim. Acta , 56 : 310 – 320 .
  • Ohloff , G. , Rautenstrauch , V. and Schulte‐Elte , K. H. 1973 . Moldellreaktionen zur Biosyntheses von Verbindungen der Damascon‐Reihe und ihre präparative Anwendung . Helv. Chim. Acta , 56 : 1503 – 1513 .
  • Azzari , E. , Faggi , C. , Gelsomini , N. and Taddei , M. 1990 . Transformation of α‐ and β‐ionones into α‐ and β‐damascone and β‐damascenone using allylsilane chemistry . J. Org. Chem. , 55 : 1106 – 1108 .
  • Fehr , C. and Galindo , G. 1986 . Synthesis of (E)‐1‐propenyl ketones from carboxylic esters and carboxamides by use of mixed organolithium‐magnesium reagents . Helv. Chim. Acta , 69 : 228 – 235 .
  • Snowden , R. L. , Linder , S. M. , Müller , B. L. and Schulte‐Elte , K. H. 1987 . β‐Cleavage of bis (homoallylic) potassium alkoxides: Two‐step preparation of propenyl ketones from carboxylic esters: Synthesis of ar‐turmerone, α‐damascone, β‐damascone and β‐damascenone . Helv. Chim. Acta , 70 : 1858 – 1878 .
  • Ayyar , K. S. , Cookson , R. C. and Kagi , D. A. 1975 . Synthesis of α‐damascone [trans‐1‐(2,6,6‐trimethylcyclohex‐3‐enyl)but‐2‐en‐1‐one] and β‐damascenone [trans‐1‐(2,6,6‐trimethylcyclohexa‐1,3‐dienyl)but‐2‐en‐1‐one] . J. Chem. Soc., Perkin Trans. 1 , : 1727 – 1736 .
  • Schulte‐Elte , K. H. , Rautenstrauch , V. and Ohloff , G. 1971 . Synthesen der stereoisomeren (+/−)‐γ‐damascone . Helv. Chim. Acta , 54 : 1805 – 1812 .
  • Dupuy , C. and Luche , J. L. 1989 . New developments of the wharton transposition . Tetrahedron , 45 : 3437 – 3444 .
  • Isoe , S. , Katsumura , S. and Sakan , T. 1973 . The synthesis of damascenone and β‐damascone and the possible mechanism of their formation from carotenoids . Helv. Chim. Acta , 56 : 1514 – 1516 .
  • Büchi , G. and Vederas , J. C. 1972 . Interchange of functionality in conjugated carbonyl compounds through isoxazoles . J. Am. Chem. Soc. , 94 : 9728 – 9732 .
  • Rautenstrauch , V. 1973 . Controlled allylic transformations via the meisenheimer rearrangement . Helv. Chim. Acta , 56 : 2492 – 2508 .
  • Sarandeses , L. A. and Luche , J. L. 1992 . A new synthesis of α‐ and β‐damascones from the ionones . J. Org. Chem. , 57 : 2757 – 2760 .
  • Naegeli , P. (Givaudan Corporation). 4‐(2,6,6‐Trimethyl‐2‐cyclohexen‐1‐ylidene)‐butan‐2‐ol. . US Patent, 4, 072, 719 . 1978 .
  • Schwab , E. and Schreier , P. 1991 . Biotransformation of β‐damascone by Botrytis cinerea . Z. Naturforsch. C: Biosci. , 46 ( 5–6 ) : 395 – 397 .
  • Schulte‐Elte , K. H. , Gautschi , F. , Renold , W. , Pauser , A. , Faukhauser , P. , Limacher , J. and Ohloff , G. 1978 . Vitispiranes, important constituents of vanilla aroma . Helv. Chim. Acta , 61 ( 3 ) : 1125 – 1133 .

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