81752-87-6Relevant academic research and scientific papers
Synthesis of three putative kairomones of the beech leaf-mining weevil Orchestes fagi (L.)
Mayo,Silk,Abeysekera,MaGee
, p. 1124 - 1132 (2016/07/21)
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.
Synthesis of (+)-Ambrein
Tanimoto, Hisahide,Oritani, Takayuki
, p. 3527 - 3536 (2007/10/03)
Enantiomerically pure (+)-Ambrein was synthesized from (+)-drimane-8,11-diol prepared via lipase catalyzed kinetic resolution, and easily prepared (i)-γ-cyclogeraniol.
Syntheses of the enantiomers of γ-cyclogeranic acid, γ-cyclocitral, and γ-damascone: Enantioselective protonation of enolates
Fehr,Galindo
, p. 539 - 552 (2007/10/02)
(R)- and (S)-γ-cyclogeranic acid ((R)- and (S)-9, resp.) were obtained by resolution of the racemate, and their absolute configurations determined by chemical correlation. The γ-acids (R)- and (S)-9 were converted into (R)- and (S)-methyl γ-cyclogeranate ((R)- and (S)-6, resp.), and (R)- and (S)-γ-damascone ((R)- and (S)-5, resp.). A more direct entry to (R)- and (S)-9 consisted in the enantioselective protonation of a thiol ester enolate with (-)- or (+)-N-isopropylephedrine ((-)- or (+)-20) and subsequent hydrolysis of the (R)- and (S)-S-phenyl γ-thiocyclogeranate ((R)- and (S)-24, resp.; 97% ee). The esters (R)- and (S)-24 were also used as precursors of (R)- and (S)-γ-damascone ((R)- and (S)-5, resp.). Alternatively, (S)-5 (75% ee) was obtained by enantioselective protonation of ketone enolate 29 with (-)-N- isopropylephedrine ((-)-20). Organoleptic evaluation demonstrated that the (S)-enantiomers of methyl γ-cyclogeranate and γ-damascone are markedly superior to their (R)-enantiomers.
Alicyclic esters and their use as perfuming ingredients
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, (2008/06/13)
The compounds of formula STR1 wherein the symbol R represents a linear or branched, saturated or unsaturated alkyl radical containing from 1 to 3 carbon atoms, are useful perfuming ingredients. They develop floral, rosy, damascone type odor notes and can
β-Cleavage of Bis(homoallylic) Potassium Alkoxides. Synthesis of γ-Damascone
Snowden, Roger L.,Linder, Simon M.
, p. 1587 - 1597 (2007/10/02)
Starting from the γ-lactone cis-1, two new syntheses of γ-damascone ((E)-4) are described.In both syntheses, the key step involves the β-cleavage of a bis(homoallylic)potassium alkoxide, viz. the transformation of 3a to 20 and (E/Z)-4, and the conversion
Synthesis of (+/-)-trixagol by an electrophilic cyclization of an allylsilane
Armstrong, Rosemary J.,Weiler, Larry
, p. 2530 - 2539 (2007/10/02)
1,5-Dienes containing an allylsilane are cyclized by Lewis acids to methylenecyclohexanes.The trimethylsilyl group exerts a strong activating and directing influence on the regioselectivity of this cyclization.The monocyclic compound 10 was converted into the diterpene, (+/-)-trixagol (3).
Electrophilic cyclization of polyene allylsylanes. Synthesis of albicanyl acetate
Armstrong, Rosemary J.,Harris, Francis L.,Weiler, Larry
, p. 673 - 675 (2007/10/02)
The allylsilanes 5 (a, R=(CH3)2CCHCH2; b, R=(CH3)2CCHCH2CH2C(CH3)CHCH2) were prepared by a nickel(II) catalyzed coupling of trimethylsilylmethylmagnesium chloride with the enol phosphate of the corresponding β-keto esters.Stannic chloride and mercuric trifluoroacetate effected a cyclization of 5.The product from 5b was converted into the marine natural product, albicanyl acetate (1).
