61315-75-1Relevant academic research and scientific papers
3-(4-Methyl-3-pentenyl)-2(5H)-furanone, alpha,alpha-acariolide and 4-(4-methyl-3-pentenyl)-2(5H)-furanone, alpha,beta-acariolide: new monoterpene lactones from the astigmatid mites, Schwiebea araujoae and Rhizoglyphus sp. (Astigmata: Acaridae).
Tarui, Hirokazu,Mori, Naoki,Nishida, Ritsuo,Okabe, Kimiko,Kuwahara, Yasumasa
, p. 135 - 140 (2002)
A new monoterpene lactone from the acarid mite, Schwiebea araujoae, was elucidated without its isolation by GC/FT-IR and GC/MS analyses to be 3-(4-methyl-3-pentenyl)-2(5H)-furanone (1) and tentatively named as alpha,alpha-acariolide. The structure of 1 was identified by its synthesis from alpha-bromo-gamma-butyrolactone via 4 reaction steps. The synthesized compound gave the same GC/MS and GC/FT-IR spectra as those of the natural product. The other monoterpene lactone was likewise elucidated from the unidentified Rhizoglyphus mite to be 4-(4-methyl-3-pentenyl)-2(5H)-furanone (2) and named as alpha,beta-acariolide; it was also identified by its synthesis in 5 reaction steps from the same butyrolactone as the starting material. GC/MS and GC/FT-IR spectra of the preparation were identical to those of the natural product.
Identification of odor-active trace compounds in blooming flower of Damask Rose (Rosa damascena)
Ohashi, Teruhisa,Miyazawa, Yamato,Ishizaki, Susumu,Kurobayashi, Yoshiko,Saito, Tsukasa
, p. 7410 - 7415 (2019)
The flower scent of the damask rose (Rosa damascena) was studied. Two ultratrace components exhibiting high flavor dilution factors were detected as odor-active compounds via aroma extract dilution analysis (AEDA). One of these had a woody note and was identified as rotundone using multidimensional gas chromatography-mass spectrometry-olfactometry (MD-GC-MS-O), while the other had a citrus note and was identified as 4-(4-methylpent-3-en-1-yl)-2(5H)-furanone (MPF) by fractionation of a commercial rose absolute from R. damascena. To the best of our knowledge, this is the first study addressing the organoleptic importance of these two compounds in the rose scent. Sensory analysis was conducted to evaluate the effects of rotundone and MPF. Adding 50 μg/kg rotundone and 5 μg/kg MPF to the aroma reconstitute of R. damascena provided it with blooming and natural characteristics. Additionally, the existence of rotundone and MPF in five types of fragrant roses was investigated.
A unified strategy for the regiospecific assembly of homoallyl-substituted butenolides and γ-hydroxybutenolides: First synthesis of luffariellolide
Boukouvalas, John,Robichaud, Jo?l,Maltais, Fran?ois
, p. 2480 - 2482 (2008/02/11)
The first synthesis of the antiinflammatory marine natural product luffariellolide has been achieved by a convergent pathway involving sp 3-sp3 cross-coupling and silyloxyfuran oxyfunctionalisation as key steps. An illustration of the inherent flexibility of this strategy is provided by a simple synthesis of α,β-acariolide and its γ-hydroxylated derivative from a common silyloxyfuran precursor. Georg Thieme Verlag Stuttgart.
A mild, efficient and general method for the synthesis of trialkylsilyl (Z)-4-oxo-2-alkenoates and γ-hydroxybutenolides
Boukouvalas, John,Lachance, Nicolas
, p. 31 - 32 (2007/10/03)
2-Trialkylsilyloxyfurans react rapidly with dimethyldioxirane at -78°C to provide trialkylsilyl (Z)-4-oxo-2-alkenoates whose hydrolysis delivers γ-hydroxybutenolides with high efficiency; a short synthesis of a naturally occurring monoterpene γ-hydroxybutenolide (4) is reported.
Reactions of α-Oxo Ketene Dithioacetals with Dimethylsulfonium Methylide: A New Versatile Synthesis of Furans and Butenolides
Okazaki, Renji,Negishi, Yoshio,Inamoto, Naoki
, p. 3819 - 3824 (2007/10/02)
The reaction of 1-mono- and 1,2-disubstituted 3,3-bis(methylthio)-2-propen-1-ones 1 with dimethylsulfonium methylide (2) affords 2,2-bis(methylthio)-2,5-dihydrofurans 3 via epoxide 8 which can be isolated in a special case.A couple of methods including acid treatment effected the conversion of 3 to 2-(methylthio)furans 4, which are found to be useful synthons of a variety of furans and butenolides.Two naturally occurring furans, perillene and rosefuran, were synthesized by this method.
SYNTHESES OF PERILLENE AND ROSEFURAN FROM COMMON STARTING MATERIALS
Takano, Seiichi,Morimoto, Masamichi,Satoh, Shigeki,Ogasawara, Kunio
, p. 1261 - 1262 (2007/10/02)
Two structurally isomeric furanomonoterpenes perillene and rosefuran have been synthesized using methallyl alcohol and prenyl chloride as common starting materials.
A NEW SYNTHESIS OF Δ2-BUTENOLIDES VIA STEREOSELECTIVE FORMATION OF α,β-ETHYLENIC ESTERS
Larcheveque, M.,Legueut, Ch.,Debal, A.,Lallemand, J. Y.
, p. 1595 - 1598 (2007/10/02)
A new synthesis of Δ2-butenolides is described which involves stereoselective condensation of an α-silyl ester anion with an α-ketoacetal.
Synthesis of Fluorinated Analogues of Geraniol
Poulter, C. Dale,Wiggins, Paul L.,Plummer, Thomas L.
, p. 1532 - 1538 (2007/10/02)
Syntheses of 3-(fluoromethyl)geraniol (4), 3-(difluoromethyl)geraniol (14), and 3-(trifluoromethyl)geraniol (20) are described.The key reaction in the routes to alcohols 4 and 20 which establishes the geranyl Z stereochemistry at the C(2)-C(3) double bond is the cis addition of (4-methylpent-3-en-1-yl)copper reagents to derivatives of ethyl 2-butynoate bearing appropriate functional groups at C(4).Attempts to prepare difluoromethyl alcohol 14 by similar routes were unsuccessful.However, the carbon skeleton of 14 was constructed by a Wittig condensation of 1,1-difluoro-6-methylhept-5-en-2-one (12) with triethyl phosphonoacetate in a reaction that yielded a 72:28 ratio of geranyl/neryl isomers.
A SIMPLE ROUTE TO Δ2-BUTENOLIDES FROM CONJUGATED ALDEHYDES
Corey, E. J.,Schmidt, Greg
, p. 731 - 734 (2007/10/02)
A variety of Δ2-butenolides may be synthesized by oxidation of the O-trimethylsilylcyanohydrins of α,β-unsaturated aldehydes using pyridinium dichromate in dimethylformamide.
