- Scalable synthesis of the aroma compounds d6-β-ionone and d6-β-cyclocitral for use as internal standards in stable isotope dilution assays
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C13 Norisoprenoids are important aroma compounds in wine, giving positive attributes to the overall wine aroma even when found at very low levels. β-Ionone is considered one of the most important aroma compounds giving violet, woody and raspberry aromas to wine, fruits and vegetables in which it is found. Due to its potent aroma at low levels, precise analytical methods are desired for its quantification. Stable isotope dilution assay (SIDA) is one of the most important of these methods but requires the use of isotopically labelled standards. Herein, we describe the scalable synthesis of d6-β-ionone and d6-β-cyclocitral, another aroma compound with smokey and fruity notes, starting from the relatively inexpensive deuterated starting material d6-acetone.
- Mosaferi, Shabnam,Jelley, Rebecca E.,Fedrizzi, Bruno,Barker, David
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- Synthesis of three putative kairomones of the beech leaf-mining weevil Orchestes fagi (L.)
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The beech leaf-mining weevil, Orchestes fagi (L.), also known as the beech flea weevil, is a common and widespread pest of beech, Fagus sylvatica L., in its native Europe. It now appears to be well established in Nova Scotia, Canada. We report a novel synthesis of 9-geranyl-p-cymene and syntheses of 9-geranyl-α-terpinene and 1,1-dimethyl-3-methylene-2-vinylcyclohexane, making partial use of known methods. All three of these compounds are found in beech leaf volatiles and/or wood and are putative kairomones of the beech leaf-mining weevil.
- Mayo,Silk,Abeysekera,MaGee
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p. 1124 - 1132
(2016/07/21)
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- Total Synthesis of (+)-Acanthodoral by the Use of a Pd-Catalyzed Metal-ene Reaction and a Nonreductive 5-exo-Acyl Radical Cyclization
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(Equation presented) The first total synthesis of the antibiotic acanthodoral (1) has been achieved from 3-methyl-2-cyclohexen-1-one in 19 steps in 2.1% overall yield. The synthesis features the use of a Pd-ene reaction in the presence of CO to form the endocyclic alkene 8, a nonreductive acyl radical cyclization reaction, and a ring contraction reaction by the Wolff rearrangement. (+)-Acanthodoral has also been synthesized starting from (+)-S-2,2-dimethyl-6-methylenecyclohexanecarboxylic acid.
- Zhang, Liming,Koreeda, Masato
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p. 537 - 540
(2007/10/03)
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- Synthesis and olfactory evaluation of (+)- and (-)-γ-ionone
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The synthesis of enantiomerically pure (+)- and (-)-γ-ionone 3 is reported. The first step in the synthesis is the diastereoisomeric enrichment of 4-nitrobenzoate derivatives of racemic γ-ionol 12. The enantioselective lipase-mediated kinetic acetylation
- Fuganti, Claudio,Serra, Stefano,Zenoni, Alessandro
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p. 2761 - 2768
(2007/10/03)
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δ-Pyronene, a terpenic synthon recently made industrially available from myrcene, has been characterized. It is an excellent raw material for the preparation of numerous intermediates used in the synthesis of perfumes and retinoids. Furthermore, new terpenic compounds including the cyclogeranyl skeleton have been prepared.
- Quirin, Marie Jeanne,Taran, Martine,Delmond, Bernard
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p. 1852 - 1856
(2007/10/03)
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- Epoxy-pyronene: Obtention of cyclocitrals from ionones and precursor of new terpenic compounds
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The selective obtention of epoxy-pyronene from δ-pyronene has been realized using metachloroperbenzoic acid. The isomerization of this epoxidic compound with Lewis and protonic acids and on active alumina has been studied leading to cyclocitrals. Ionones are obtained from epoxy-pyronene by homologation with various C3 units, in the presence of paratoluenesulfonic acid in order to obtain β-cyclocitral in situ. New terpenic compounds with the cyclogeranyl skeleton were obtained from epoxy-pyronene by reduction followed by homologation.
- Marc,Soulet,Serramedan,Delmond
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p. 3381 - 3388
(2007/10/02)
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The selective obtention of epoxides from delta-pyronene has been realized using a peracid and a cyclodehydrohalogenation reaction. The isomerization of an epoxidic isomer with Lewis and protonic acids and on active alumina has been studied leading to cyclocitrals.
- Serramedan
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p. 4457 - 4460
(2007/10/02)
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- Cyclic ketones and their use as perfuming ingredients
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Novel compounds of formula STR1 wherein the dotted lines indicate the location of a single or double bond, symbol R1 stands for a hydrogen atom or a methyl radical, symbol R2 represents a linear or branched, saturated or unsaturated, C1 to C4 alkyl radical, provided that R1 is not hydrogen when R2 represents a methyl or n-propyl radical and the ring is saturated. Compounds (Ia) are useful as perfuming ingredients. A process for their preparation is disclosed.
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- Reaction of Ester Enolates with Nucleophiles. Stereocontrolled Formation of Ketone and Aldehyde Enolates
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Lithium enolates of carboxylic and thiocarboxylic esters react with nucleophiles to afford ketone and aldehyde enolates and subsequently their enol silyl ethers diastereoselectively.This reaction is applied to the synthesis of γ-damascone, α-damascone, β-safranal, and artemisia ketone.
- Fehr, Charles,Galindo, Jose
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p. 1828 - 1830
(2007/10/02)
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- SYNTHESE PRATIQUE DU γ-CYCLOCITRAL
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A simple and practical synthesis of the title compound 1 starting with N,N-dimethyl-aminoacetonitrile 2 and 1-bromomethyl-3,3-dimethylcyclohexene 3 is described.
- Stella, Lucien
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p. 3457 - 3458
(2007/10/02)
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- Sulphone-based Elimination Reactions in Synthesis. Part 2. Diumycinol
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Diumycinol , a hydrolytic product of the antibiotic diumycin, was assembled from three fragments: 1-(2-phenylsulphonylethyl)-2-methylene-6,6-dimethylcyc
- Kocienski, Philip,Todd, Michael
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p. 1783 - 1789
(2007/10/02)
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- Rearrangement of Allylic Silylsulphonium Ylides. A Synthesis of βγ-Unsaturated Aldehydes
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The ylides derived from the reaction of allylic silylmethylsulphonium salts with n-butyl-lithium rearrange to homoallylic α-methylthiosilanes which are precursors to βγ-unsaturated aldehydes.
- Kocienski, Philip J.
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p. 1096 - 1097
(2007/10/02)
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