24048-52-0

Upstream product

• 126-91-0 linalool 
• 126-90-9 (S)-(+)-linalool 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 

Relevant academic research and scientific papers

Biotransformations of terpenes by fungi from amazonian Citrus plants

The biotransformations of (RS)-linalool (1), (S)-citronellal (2), and sabinene (3) with fungi isolated from the epicarp of fruits of Citrus genus of the Amazonian forest (i.e., C. limon, C. aurantifolia, C. aurantium, and C. paradisiaca) are reported. The

Vanadium(V)-catalyzed oxidation of (3R)-linalool - The selective formation of furanoid linalool oxides and their conversion into isocyclocapitelline derivatives

Oxidation of (3R)-linalool (2) with tert-butyl hydroperoxide (TBHP) occurs at the 6,7-position to selectively afford linalool oxide cis-1, if catalyzed by vanadium(V) Schiff base complexes 4. Substituted tetrahydrofuran cis-1 and its isomer trans-1 served

(Schiff-base)vanadium(v) complex-catalyzed oxidations of substituted bis(homoallylic) alcohols - Stereoselective synthesis of functionalized tetrahydrofurans

Vanadium(v) complexes 4 have been prepared from tridentate Schiff-base ligands 3 and VO(OEt)3. All vanadium(v) compounds were characterized (IR, UV/Vis, and 51V NMR spectroscopy, and in selected examples by X-ray diffraction analysis) and were applied as oxidation catalysts for the stereoselective synthesis of functionalized tetrahydrofurans 2 starting from substituted bis(homoallylic) alcohols 1 (mono- or trisubstituted C-C double bonds). Oxidation of secondary or tertiary 1-alkyl-, 1-vinyl-, or 1-phenyl-substituted 5,5-dimethyl-4-penten-1-ols under optimized conditions [TBHP as primary oxidant and 1,2-(amino)indanol-derived vanadium(v) reagent 4g as catalyst] provided 2,5-cis-configured tetrahydrofurans in synthetically useful yields and diastereoselectivities (22-96% de). On the other hand, trans-disubstituted oxolanes (62%-96 de) were obtained from oxidations of 2- or 3-alkyl- and 2- or 3-phenyl-substituted 5,5-dimethyl-4-penten-1-ols bis(homoallylic) allyhc) alcohols. Treatment of 4-penten-1-ols (i.e. substrates with monosubstituted olefinic π-bonds) with TBHP and catalytic amounts of vanadium(v) complex 4g furnished trans-disubstituted tetrahydrofurans as major products (20-96% de), no matter whether an alkyl or a phenyl substituent was located in position 1, 2, or 3 of the alkenol chain. The mechanism of this reaction has been investigated in detail. Based on results from 51V NMR spectroscopy and competition kinetics, it proceeds by a transition metal-peroxy pathway. In an initial step, TBHP coordinates to, for example, N-(2-oxidophenyl)salicylideniminato-derived vanadium complex 4a. Subsequent alkenol binding gives rise to a "loaded" vanadium(v) peroxy complex (e.g. 60) which facilitates diastereoselective oxygen transfer, presumably onto a coordinated substrate. This step leads to the formation of functionalized tetrahydrofurans as major products. TBHP binding to the remaining vanadium(v) complex then allows a regeneration of the active oxidant, for example peroxy complex 57. The origin of the observed diastereoselectivity in this oxidation has been studied in an independent stereochemical analysis. Thus, diastereomerically enriched epoxy alcohol (1R,4R)-10 was prepared. Its treatment with 1,2-(amino)indanol-derived vanadium complex 4g affords a 91:9 mixture of cis-2-(1-hydroxy-1-methylethyl)-5-(phenyl)tetrahydrofuran (cis-6) and cis-2,2-dimethyl-6-(phenyl)tetrahydropyran-3-ol (cis-7). Similarly, a 39:61 mixture of heterocycles trans-6 and trans-7 was obtained from epoxy alcohol (1S,4R)-10, if treated with Lewis acid 4g. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

The Use of Acyclic Monoterpenes in the Preparation of β-pyrones; Synthesis of the Right-hand Fragment of Usneoidone E

The right hand fragment, 36, of Usneoidone E, 1, a powerful antiviral and antitumoural agent has been synthesized from the β-pyrone 32.Using lanalool as starting material, a 2,2,6,6-tetrasubstituted dihydropyrane 20, precursor of 32 and 33, was prepared. 20 was also synthesized from geranyl acetate through selenide 7, and is a versatile precursor for the synthesis of tetraprenyltoluquinols.Unambiguous 13C NMR assignment has been done by 2D correlations.

Optical Isomers of Linalool and Linalool Oxides in Tea Aroma

The main aroma components of oolong and black tea, linalool and four diastereomers of linalool oxides (LOs), were enantioselectively isolated by capillary gas chromatography, using a column coated with an optically active liquid phase, permethylated β-cyclodextrin.The R/S ratio varied among linalool and LOs, and among the different types of tea, the ratio for a particular compound also being different.However, the complete patterns of R/S ratio were similar in the semi-fermented and fermented teas, respectively.Using a specific cultivar of black tea, the R/S ratio for each of the five compounds was compared in the free state in black tea with that of an aglycone of the glycoside in fresh tea leaves or in black tea.While the e.e. values of the compounds varied, those for a specific compound were similar, except for linalool, regardless of their free or combined state.These results show that POs are not directly transformed from linalool, but are formed enzymatically from glycoside precursors.