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Search for "monoterpene" in Full Text gives 38 result(s) in Beilstein Journal of Organic Chemistry.
A detailed view on 1,8-cineol biosynthesis by Streptomyces clavuligerus
Beilstein J. Org. Chem. 2016, 12, 2317–2324, doi:10.3762/bjoc.12.225
- monooxygenases and acyl transferases [12][13]. Very few cases are known in which terpene cyclases generate an achiral product as exemplified by the monoterpene 1,8-cineol (eucalyptol, 1) and the sesquiterpenes germacrene B (2) and α-humulene (3) (Figure 1). A direct 1,6-cyclisation of the monoterpene precursor
- distinguished based on the labelling experiments described here. Discussion Plant and bacterial terpene cyclases show important structural differences [33]. While plant monoterpene synthases are composed of α and β domains and exhibit a quarternary α2β2 structure [34][35], bacterial mono- and sesquiterpene
The direct oxidative diene cyclization and related reactions in natural product synthesis
Beilstein J. Org. Chem. 2016, 12, 2104–2123, doi:10.3762/bjoc.12.200
- considered in complement [4][5][6]. Oxidative cyclization – Historical background In 1924 Kötz and Steche reported on an investigation of the constitution of the monoterpene geraniol (1, R = H) [7]. Though the overall structure was known at that time, the position of one of the two C–C-double bonds within
Mechanistic investigations on six bacterial terpene cyclases
Beilstein J. Org. Chem. 2016, 12, 1839–1850, doi:10.3762/bjoc.12.173
- interesting molecular properties. Particularly obvious is their often characteristic aroma that contributes to the typical flavour of many essential oils from plants. This is exemplified by the monoterpene α-pinene that occurs in form of both enantiomers in pine trees, while (R)-(+)-limonene is found in
- much later, with the first described compounds being geosmin [3] and 2-methylisoborneol [4], two irregular terpenoids that represent a degraded sesquiterpene [5] and a methylated monoterpene [6], respectively. These compounds have a musty or earthy aroma and are responsible for the smell of freshly
Selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene
Beilstein J. Org. Chem. 2016, 12, 1361–1365, doi:10.3762/bjoc.12.129
- homoallylic alcohol. Critical factors for optimization of this reaction are highlighted. The utility of the product bromochloride is demonstrated by the first total synthesis of an antibacterial polyhalogenated monoterpene, (−)-anverene. Keywords: enantioselective catalysis; halogenation; natural products
Efficient syntheses of climate relevant isoprene nitrates and (1R,5S)-(−)-myrtenol nitrate
Beilstein J. Org. Chem. 2016, 12, 1081–1095, doi:10.3762/bjoc.12.103
- monoterpene nitrate (1R,2S)-(−)-myrtenol nitrate. Keywords: atmospheric chemistry; exchange reaction; halide; isoprene nitrate; monoterpene; Introduction Understanding the chemistry of the biosphere and its interaction with the atmosphere is fundamental to Earth System science. Such is the importance of
- monoterpenes account for a large percentage of the total emissions that are not non-methane VOCs. Furthermore although monoterpene emissions (127 Tg C yr−1) are significant lower than isoprene [6] (viz. 600 Tg C yr−1) they are nonetheless gaining in significance and are now considered to be important
- to monoterpene derived O-nitrate ester synthesis was undertaken using (1R,5S)-(−)-myrtenol (84) which was quickly and efficiently converted into the corresponding optically active 1° alkyl bromide 85 which, due to its instability, was used ‘as is’ [55]. Employing our standard silver nitrate
A practical way to synthesize chiral fluoro-containing polyhydro-2H-chromenes from monoterpenoids
Beilstein J. Org. Chem. 2016, 12, 648–653, doi:10.3762/bjoc.12.64
- -fluorohexahydro-2H-chromenes under the developed conditions, the reaction occurs with inversion of configuration. Keywords: chirality; fluorine; halo-Prins reaction; isopulegol; monoterpene; Introduction Recently, we have found that a reaction between para-mentha-6,8-dien-2,3-diol (1) and aromatic aldehydes in
Thermal and oxidative stability of the Ocimum basilicum L. essential oil/β-cyclodextrin supramolecular system
Beilstein J. Org. Chem. 2014, 10, 2809–2820, doi:10.3762/bjoc.10.298
- properties, and its antimicrobial [19] biological effects. Moreover, the anticancer potential of basil components has been studied [24]. These sensory and pharmaceutical properties of basil are primarily due to the presence of essential oil components, which consist of monoterpene hydrocarbons (e.g., β
- %) and methylchavicol (6) (19.6%), from oxygenated monoterpene and phenolic derivative compound classes, respectively. Limonene (1) was the most important component from the monoterpene class (0.5%), while other monoterpene derivatives in the O. basilicum L. essential oil were eucalyptol (2), camphor (5
Stereoselective synthesis of perillaldehyde-based chiral β-amino acid derivatives through conjugate addition of lithium amides
Beilstein J. Org. Chem. 2014, 10, 2738–2742, doi:10.3762/bjoc.10.289
- addition was observed. Amino ester 11 was obtained as a single product and transformed to the corresponding amino acids 10A and 10D in good yields on the gram scale. Keywords: asymmetric synthesis; β-amino acid; chiral; Michael addition; monoterpene; Introduction In the past decade, cyclic β-amino acids
- ][34]. From this aspect, chiral, monoterpene-based α,β-unsaturated esters might be excellent starting materials, in which the natural monoterpene skeleton may serve as the chiral origin for the stereoselective construction of the β-amino acid moiety. Our present aim was the synthesis of new, limonene
Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules
Beilstein J. Org. Chem. 2014, 10, 1848–1877, doi:10.3762/bjoc.10.195
- inflammation and traumatic bleeding. The leaves and stems of this plant contain oleoside-type secoiridoid glucosides with structurally interesting tetrasubstituted cyclopentanoid monoterpene units [116]. Two representative examples of these glycosides are nudifloside A (151) and D (13), which share a common
Selective allylic hydroxylation of acyclic terpenoids by CYP154E1 from Thermobifida fusca YX
Beilstein J. Org. Chem. 2014, 10, 1347–1353, doi:10.3762/bjoc.10.137
- hydroxylation reactions leading to synthetically relevant intermediates [5][6][7][8][9][10][11]. In addition to chemical catalysts a range of enzymes has been studied for selective allylic hydroxylation of alkenes [12][13]. Among biosynthetic routes selective allylic hydroxylation of monoterpene olefines to
Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics
Beilstein J. Org. Chem. 2014, 10, 544–598, doi:10.3762/bjoc.10.50
- -3CR-approach with enantiopure monoterpene-based β-amino acids [43] (19, Scheme 8), giving 22 as major isomer [44]. The stereoselectivity for 22 was explained by the steric effects of the dimethyl bridge that might prefer a Re-attack of the isocyanide. Compared to methanol, again the reaction in water
A new intermediate in the Prins reaction
Beilstein J. Org. Chem. 2013, 9, 476–485, doi:10.3762/bjoc.9.51
- produced when pinene (a bicyclic monoterpene) was heated with paraformaldehyde. However, Prins performed the first rather comprehensive study of the reactions between formaldehyde and hydrocarbons with C=C double bonds [2][3]. These were styrene, pinene, camphene and anethole. As a catalyst, sulfuric acid
Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones
Beilstein J. Org. Chem. 2012, 8, 1246–1255, doi:10.3762/bjoc.8.140
- analysis (GC/CIMS) showed the molecular mass of the compound to be M+ = 168, while high resolution mass spectrometry (GC/HRMS) proved its atomic composition to be C10H16O2, suggesting an oxygenated monoterpene as the target structure. The fragmentation pattern, exhibited in the 70 eV EI-mass spectrum
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