- Rosin-based acid anhydrides as alternatives to petrochemical curing agents
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In this paper, two bio-based epoxy curing agents were synthesized using rosin acids. The chemical structures of the rosin derivatives were confirmed in detail by 1H NMR, 13C NMR, FT-IR and ESI-MS. The synthesis methods of the rosin-based curing agents, curing behaviors and properties of the cured epoxy resins were studied. Two commercial curing agents, which have similar functionality and structural resemblance to the rosin-based curing agents, were also used in the study for comparison. Compared with the synthesis of petrochemical curing agents, the synthesis of rosin-based curing agents was simpler and more environmentally friendly, and has less strict requirements on reactors and catalysts. Non-isothermal curing of a commercial liquid epoxy was studied using differential scanning calorimetry (DSC). The thermal mechanical properties and thermal stability of the cured epoxy resins were evaluated using dynamic mechanical analysis (DMA) and thermogravimetric analysis (TGA), respectively. Results showed that the curing behaviors of the rosin-based curing agents were similar to those of the commercial curing agents. The epoxies cured by rosin-based curing agents also demonstrated similar thermal mechanical properties and thermal stability to the epoxies cured by commercial curing agent analogs.
- Liu, Xiaoqing,Xin, Wenbo,Zhang, Jinwen
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- Efficient syntheis of the key intermediate triptophenolide methyl ether for the synthesis of(-)-triptolide
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An efficient synthesis of triptophenolide methyl ether 4 from the readily available abietic acid 3 in nine steps is described and successfully applied to the synthesis of (-)-triptolide 1.The route is of characteristic of low cost, high yield and easy operation.In addition, every reaction in this route has been successfully scaled-up to a 100 g substrate level without loss of yield.
- Zhou, Bing,Li, Xiaomei,Feng, Huijin,Li, Yuanchao
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- Cytotoxic, immunomodulatory, antimycotic, and antiviral activities of semisynthetic 14-hydroxyabietane derivatives and triptoquinone C-4 epimers
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A series of C14-hydroxy derivatives of dehydroabietic acid were synthesised from commercial abietic acid and evaluated for their cytotoxic, antimycotic, and antiviral activities. From these C14-hydroxy derivatives, triptoquinone C-4 epimers were obtained and their immunomodulatory activity was additionally evaluated. None of the tested compounds showed antiviral activity against herpes simplex virus type 1 (HHV-1), and nor did they display antimycotic activity against certain Aspergillus, spp. except for one compound, abieta-8,11,13-trien- 14,18-diol. Interestingly, two triptoquinone epimers showed cytotoxic activity, and one of them induced mitochondrial potential loss, DNA damage and cell cycle distribution alterations in Jurkat cells, but not in human peripheral blood mononuclear cells. In addition, these compounds inhibited monocyte's differentiation and production of pro-inflammatory cytokines, IL-1β and TNF-α, and the anti-inflammatory cytokine IL-10 in the presence of LPS. In conclusion, one of the triptoquinone molecules could be a promising scaffold for the development of novel anti-cancer agents, and two of them could be potential anti-inflammatory agents. The Royal Society of Chemistry.
- Zapata, Bibiana,Rojas, Mauricio,Betancur-Galvis, Liliana,Mesa-Arango, Ana Cecilia,Perez-Guaita, David,Gonzalez, Miguel A.
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- Research into the oxidation of abietic acid–derived enone with atmospheric oxygen
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This work presents results of methyl 7-oxoabiet-13(14)-en-18-oate (3) self-oxidation with air-oxygen in the presence of various bases such as triethylamine or sodium t-butoxide. While under aerobic conditions, the use of sodium t-butoxide as a base results in the formation of four isomeric alcohols, an addition of triethylamine into reaction medium directs the enone 3 oxidation to hydroperoxides. To clarify this base dependence and to obtain more in-depth information about this reaction additional studies with cyclohexenone as a reference enone have been undertaken. Their results demonstrated the predisposition of abietane hydroperoxides to oxidize α,β-unsaturated ketones to epoxides in the presence of t-butoxide while reducing the hydroperoxide group to hydroxyl. This ability of hydroperoxides to epoxidize conjugated double bonds and confirmed by the present study intermolecular course allowed proposing a plausible mechanism for this reaction.
- Masnyk, Marek,Ku?mirek, Damian,Trzybiński, Damian,Frelek, Jadwiga
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- Phytoalexin-like Activity of Abietic Acid and Its Derivatives
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Abietic acid and some of its derivatives, not known to be naturally occurring phytoalexins, were examined for their ability to promote H+ conductance across membranes and to inhibit growth of two fungal species-Aphanomyces euteiches and Fusarium moniliforme.These results were compared with those of phaseollin, at phytoalexin isolated from kidney beans.Ion leakage and fungal growth inhibition were shown to be a function of structure, results that suggest that pterocarpan phytoalexin activity requires the presence of a polar, protic functional group situated at the end of a large, rigid hydrophobic moiety.Log P values for phaseollin, abietic acid, and some derivatives of abietic acid were also determined. Keywords: Abietic acid; H+ leakage; antifungal activity; log P; phaseollin
- Spessard, Gary O.,Matthews, David R.,Nelson, Michael D.,Rajtora, Tim C.,Fossum, Michael J.,Giannini, John L.
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- Synthesis and biological evaluation of abietic acid derivatives
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A series of C18-oxygenated derivatives of abietic acid were synthesized and evaluated for their cytotoxic, antimycotic, and antiviral activities. In general, the introduction of an aldehyde group at C18 did improve the resultant bioactivity, while the presence of an acid or alcohol led to less active compounds.
- Gonzalez, Miguel A.,Correa-Royero, Julieth,Agudelo, Lee,Mesa, Ana,Betancur-Galvis, Liliana
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- Synthesis of new chiral synthons through regioselective ozonolysis of methyl abietate
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The regioselective ozonolysis of methyl abietate to a stable epoxy- ozonide is described.
- Dos Santos, Catarina,De Rosso, César R.S.,Imamura, Paulo M.
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- Identification of 15-hydroperoxyabietic acid as a contact allergen in Portuguese colophony
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15-Hydroperoxyabietic acid (15-HPA) has been isolated from Portuguese colophony of the gum rosin type and identified as its methyl ester. The structure of the compound was elucidated using UV, IR, NMR and mass sepctrometry. 15-HPA methyl ester was found to be an elicitor when tested in colophony-sensitized guinea-pigs. The sensitizing capacity was verified in the same species and 15-HPA methyl ester was considered to be a strong allergen. The eliciting potential was also verified in patients with known allergy to colophony. The Portuguese gum rosin investigated contained approximately 1% of 15-HPA. Based on its allergenicity and the amounts isolated, we conclude that 15-HPA is a main contact allergen in Portuguese gum rosin.
- Karlberg,Bohlinder,Boman,Hacksell,Hermansson,Jacobsson,Nilsson
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- Synthesis of complex and diverse compounds through ring distortion of abietic acid
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Many compound screening collections are populated by members that possess a low degree of structural complexity. In an effort to generate compounds that are both complex and diverse, we have developed a strategy that uses natural products as a starting point for complex molecule synthesis. Herein we apply this complexity-to-diversity approach to abietic acid, an abundant natural product used commercially in paints, varnishes, and lacquers. From abietic acid we synthesize a collection of complex (as assessed by fraction of sp 3-hybridized carbons and number of stereogenic centers) and diverse (as assessed by Tanimoto analysis) small molecules. The 84 compounds constructed herein, and those created through similar efforts, should find utility in a variety of biological screens. Abietic acid was used as the starting point for the synthesis of 84 complex and diverse small molecules. Their complexity was assessed by the fraction of sp3-hybridized carbon atoms and the number of stereogenic centers, and their diversity was evaluated by Tanimoto analysis. The 84 compounds constructed herein, and those created through similar efforts, should find utility in a variety of biological screens. Copyright
- Rafferty, Ryan J.,Hicklin, Robert W.,Maloof, Katherine A.,Hergenrother, Paul J.
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- A New Synthesis of Desmethylambraoxide
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A new synthesis of the title compound starting from abietic acid is described.Regioselective osmylation of the Δ13,14-double bond of abietic acid methyl ester (6) and subsequent hydrogenation furnishes dihydrodihydroxyabietic acid methyl ester (12) with an all-trans-connection of the three rings.Periodate cleavage of 12 leads to 13 which can be transformed into the triester 14 by Baeyer-Villiger oxidation.The configuration of the aldehyde group in 13 as well of the formyloxy group in 14 has been ensured to be equatorial.LAH-reduction of 14 leads to the triol 16 which after cyclisation and reductive dehydroxylation furnishes the fragrance compound 4. - Keywords: Abietic acid; Ambergris fragrance compound; Baeyer-Villiger oxidation; Decahydro-1-naphthalene-carboxylic acid derivatives; Dodecahydro-1H-naphthopyrane derivatives; Periodate cleavage; Reductive dehydroxylation; Regioselective osmylation
- Buchbauer, Gerhard,Heneis, Vera M.,Krejci, Viktoria,Talsky, Claudia,Wunderer, Hanneliese
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- Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction
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The first synthesis of C-18- and C-19-bifunctionalized abietane diterpenoids, bodinieric (or callicapoic) acids, via an aldol reaction has been developed. This key aldol reaction was very sensitive to steric hindrance. This fact has been studied by deuterium exchange experiments and DFT methods. Optimization of this reaction led to the synthesis of anti-inflammatory bodinieric acids A and B, starting from abietic acid.
- González-Cardenete, Miguel A.,Zaragozá, Ramón J.
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p. 15015 - 15022
(2020/04/27)
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- Studies on the [2+3] cycloaddition reaction of nitrile oxides to abietic acid esters
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[2+3] Dipolar cycloadditions of aromatic nitrile oxides to abietic acid esters were investigated. The reactions showed complete site selectivity and regioselectivity, while the stereoselectivity depended on the structures of the dipolarophiles.
- Gucma, Miros?aw,Go??biewski, W. Marek,?elechowski, Krzysztof,Krawczyk, Maria
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p. 1073 - 1081
(2019/11/19)
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- Late-stage C-H amination of abietane diterpenoids
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This study aims at highlighting the synthetic versatility of the rhodium-catalyzed C-H amination reactions using iodine(iii) oxidants for the late-stage functionalization of natural products. Inter-and intramolecular nitrene insertions have been performed from various abietane diterpenoids, leading to the amination of the C-3, C-6, C-7, C-11 and C-15 positions. Ca. 20 aminated compounds have been isolated with yields of up to 86% and high levels of regio-, chemo-and stereoselectivities.
- Lapuh, María Ivana,Dana, Alejandro,Di Chenna, Pablo H.,Darses, Benjamin,Durán, Fernando J.,Dauban, Philippe
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supporting information
p. 4736 - 4746
(2019/05/24)
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- Synthesis and Biological Studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and Representative Analogues: SAR Studies
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The first semisynthesis and biological profiling of the new abietane diterpenoid (+)-liquiditerpenoic acid A (abietopinoic acid) (7) along with several analogues are reported. The compounds were obtained from readily available methyl dehydroabietate (8), which was derived from (-)-abietic acid (1). Biological comparison was conducted according to the different functional groups, leading to some basic structure-activity relationships (SAR). In particular, the ferruginol and sugiol analogues 7 and 10-16 were characterized by the presence of an acetylated phenolic moiety, an oxidized C-7 as a carbonyl, and a different functional group at C-18 (methoxycarbonyl, carboxylic acid, and hydroxymethyl). The biological properties of these compounds were investigated against a panel of six representative human tumor solid cells (A549, HBL-100, HeLa, SW1573, T-47D, and WiDr), five leukemia cellular models (NALM-06, KOPN-8, SUP-B15, UoCB1, and BCR-ABL), and four Leishmania species (L. infantum, L. donovani, L. amazonensis, and L. guyanensis). A molecular docking study pointed out some targets in these Leishmania species. In addition, the ability of the compounds to modulate GABAA receptors (α1β2γ2s) is also reported. The combined findings indicate that these abietane diterpenoids offer a source of novel bioactive molecules with promising pharmacological properties from cheap chiral-pool building blocks.
- Hamuli?, Damir,Stadler, Marco,Hering, Steffen,Padrón, José M.,Bassett, Rachel,Rivas, Fatima,Loza-Mejía, Marco A.,Dea-Ayuela, M. Auxiliadora,González-Cardenete, Miguel A.
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supporting information
p. 823 - 831
(2019/03/19)
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- Synthesis of 4- epi-Parviflorons A, C, and E: Structure-Activity Relationship Study of Antiproliferative Abietane Derivatives
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The first syntheses of 4-epi-parviflorons A, C, and E (4-epi-1-3) were achieved in 12-13 steps from commercially available (-)-abietic acid (5). All synthesized compounds, including intermediates and derivatives, were evaluated for antiproliferative activity against five human tumor cell lines. A structure-activity relationship study revealed no significant difference between Pf E and 4-epi-Pf E, the importance of two oxygen functional groups at C-11 and C-12 for antiproliferative activity, as well as a combination of carbomethoxy at C-4 and a benzoyl ester with electron-drawing group at C-12 or hydroxymethyl at C-4 and an appropriate oxidation state of ring-B/C for triple-negative breast cancer cell selectivity.
- Miyajima, Yui,Saito, Yohei,Takeya, Munehisa,Goto, Masuo,Nakagawa-Goto, Kyoko
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- In depth analysis of chiroptical properties of enones derived from abietic acid
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With the use of inexpensive commercially available abietic acid, a whole series of abietane enones were prepared in high yields. The structures of all the products obtained were determined by comprehensive spectroscopic analysis with particular emphasis on the use of advanced NMR techniques, comparison with previously reported data and, where possible, by single crystal X-ray diffraction. However, in cases where X-ray crystallography was not applicable or compounds tested were unstable, a final stereochemical assignment could be inferred only by electronic circular dichroism (ECD) supported by vibrational circular dichroism to increase credibility. To reveal the relationship between structure and chiroptical properties, we used combined experimental and theoretical analysis of geometries, structural parameters, and chiroptical properties of all enones synthesized. A thorough analysis of their conformational flexibility by examining the effect of solvent and temperature on the ECD spectra was also used to achieve desired objectives. As a result, the impact of substituents adjacent to the enone chromophore on the conformation was determined by demonstrating that even slight changes in the position of hydroxyl and isopropyl groups attached to carbon C13 may substantially affect ECD curves' pattern, leading in some cases to Cotton effects sign reversal.
- Masnyk, Marek,Butkiewicz, Aleksandra,Górecki, Marcin,Luboradzki, Roman,Paluch, Piotr,Potrzebowski, Marek J.,Frelek, Jadwiga
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p. 3547 - 3561
(2018/04/14)
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- A rosinyl imidazoline compound and its synthetic method and application
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The present invention relates to the technical field of synthesis and application of compounds used in the metal corrosion, and specifically discloses a novel rosinyl imidazoline compound and a synthesis method and application thereof. A starting raw material of the rosinyl imidazoline compound is rosin acid, the raw material is single, and a synthesis route and operation are simple. The method for preparation of an inhibitor from the synthesized compound is simple, and the inhibitor can be prepared only by dissolving the compound in dimethyl formamide, after the compound is dissolved in the dimethyl formamide completely, dissolving in water, and evenly mixing. This inhibitor is safe and environmentally-friendly, has excellent corrosion inhibition effect, and can be used for oil and gas field ground gathering and transportation pipelines to prevent corrosive gas corrosion damage to steel gas and other metal materials, and reduce the corrosion losses.
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Paragraph 0010; 0030; 0032-0033
(2017/08/26)
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- Methyl esterification method of low-toxicity rosin-resin acid
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The invention discloses a methyl esterification method of low-toxicity rosin-resin acid, comprising the following steps: mixing rosin-resin acid and methyl esterification reagent dimethyl carbonate, dissolving in an organic solvent, and reflux reacting at 68-110 DEG C in the presence of a base catalyst for 24-72 h to obtain methyl rosinate-resinate. The methyl rosinate-resinate prepared by the method has yield up to 99.6%, the method has the advantages that materials are easy to obtain, the preparation process is safe, the materials are low in toxicity, and reacting is easy to control and post-treatment is simple and easy.
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Paragraph 0022; 0023; 0024; 0025; 0026; 0027; 0028-0032
(2016/12/01)
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- Novel rosin imidazoline corrosion inhibitor
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The invention relates to the synthesis and application technology field of compounds used for metal anticorrosion, and concretely discloses a novel rosin imidazoline corrosion inhibitor, a synthetic method and applications. The initial raw material of the provided compound is rosin acid, the raw material is single and the synthetic route operation is simple. The method for preparing a corrosion inhibitor from the synthesized compound is simple, the compound is dissolved in dimethyl formamide, then the obtained solution is dissolved in water, then 1-hydroxyethylidene-1,1-diphosphonic acid is added, and uniform stirring is carried out. The corrosion inhibitor is safe and environmentally friendly, and has excellent corrosion inhibition effects. The corrosion inhibitor can be used for oil and gas field ground gathering and storage and transportation pipes, prevents damage of corrosive gases to metal materials of steel and the like and reduces corrosion loss.
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Paragraph 0009; 0024-0027
(2017/03/18)
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- Mild method for the selective esterification of carboxylic acids based on the Garegg-samuelsson reaction
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A mild method for the selective esterification of primary alcohols is described. The use of different phosphines, I2, and imidazole allows the selective esterification of a wide variety of acids with excellent results. The generation of a bulky phosphonium-carboxylate salt as intermediate could justify the selectivity observed in this process. Additionally, amides also can be synthesized with use of this method.
- Morcillo, Sara P.,Alvarez De Cienfuegos, Luis,Mota, Antonio J.,Justicia, Jose,Robles, Rafael
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experimental part
p. 2277 - 2281
(2011/05/19)
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- Synthesis and biological evaluation of dehydroabietic acid derivatives
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A series of C18-oxygenated derivatives of dehydroabietic acid were synthesized from commercial abietic acid and evaluated for their cytotoxic, antimycotic, and antiviral activities.
- Gonzalez, Miguel A.,Perez-Guaita, David,Correa-Royero, Julieth,Zapata, Bibiana,Agudelo, Lee,Mesa-Arango, Ana,Betancur-Galvis, Liliana
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scheme or table
p. 811 - 816
(2010/04/26)
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- ROSIN DERIVED EPOXIDES AND CURING AGENTS
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An epoxide agent for an epoxy resin system, the epoxide agent comprising at least one non-acid functional rosin moiety and at least one epoxide moiety. Another embodiment is a curing agent for an epoxy resin system comprising at least one non- acid functional rosin moiety and at least one moiety that is reactive with an epoxy.
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Page/Page column 23-24
(2010/04/25)
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- Synthesis of an ambergris-type ketal from abietic acid
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Abietic acid, the main component of pine rosin, was used as starting material for the hemisynthesis of the ambergris-type ketal. The key intermediate step consisted of the synthesis of an exocyclic olefin through appropriate handling of a very sensitive aldehyde generated as an intermediate precursor. Georg Thieme Verlag Stuttgart.
- Costa, M. Ceu,Alves,Correia, M. Eduarda,Marcelo-Curto, M. Joao
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p. 1171 - 1175
(2007/10/03)
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- Trimethylsilyldiazomethane - A mild and efficient reagent for the methylation of carboxylic acids and alcohols in natural products
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Esterification of various naturally occurring carboxylic acids with trimethylsilyldiazo-methane proceeds nearly quantitatively under very mild conditions. Furthermore, highly sterically hindered alcohols can be converted directly to the corresponding methyl ethers. Improved methods for the preparation and quantification of this reagent are described. Springer-Verlag 2004.
- Presser, Armin,Huefner, Antje
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p. 1015 - 1022
(2007/10/03)
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- Synthesis and characterization of abietadiene, levopimaradiene, palustradiene, and neoabietadiene: Hydrocarbon precursors of the abietane diterpene resin acids
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The abietane diterpenes - abietadiene, levopimaradiene, palustradiene, and neoabietadiene (1b-4b) - were prepared from the corresponding resin acids by diazomethane esterifications, LiAlH4 reductions, tosylations, and Zn/NaI reductions. Abietadiene was also obtained less efficiently by catechol borane reduction of abietadienal tosylhydrazone and Li/NH3 reduction of its 18-phenylthio derivative. These conjugated dienes were characterized by chromatographic properties (HPLC, TLC, GC), MS fragmentation patterns, optical rotations, and UV, IR, 1H NMR, and 13C NMR data. Assignments for the 1H and 13C NMR spectra were made by COSY, DEPT, HMQC, HMBC, NOE data, H-H coupling analysis, and comparisons with literature data. The four diterpenes were identified as cyclization products of recombinant abietadiene synthase, supporting their likely role in the biosynthesis of the abietane resin acids in conifer oleoresin.
- Lee, Hyung-Jae,Ravn, Matthew M.,Coates, Robert M.
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p. 6155 - 6167
(2007/10/03)
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- Diterpenoid carboxylic acid anhydrides of the abietane, pimarane, and isopimarane series
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Methods were developed for preparation of diterpenoid carboxylic acid anhydrides of the abietane, pimarane, and isopimarane series, the corresponding mixed anhydrides, and mixed anhydrides derived from resin acids and organic or inorganic acids. The resulting anhydrides sharply differ from the parent acids in physical properties; their thermal reactions and isomerizations and the rates of formation and hydrolysis were studied. The data obtained were used to develop new procedures for separation of anhydride mixtures into pure components. Reactions of abietic anhydride with some nucleophilic reagents gave the corresponding esters, ketones, amides, etc. Commercial samples of pine wood resins (gum rosin and tallic rosin) were shown to contain a small amount (0.2%) of diterpenoid anhydride mixtures.
- Bardyshev
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- REACTIONS OF DITERPENOIDS ON SOLID SUPPORTS. I. OXIDATION OF METHYL ABIETATE ON THE SORBENTS Al2O3 AND SiO2 CONTAINING POTASSIUM PERMANGANATE
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The oxidation of methyl abietate on the sorbents Al2O3 and SiO2 containing potassium permanganate has benn studied.It has been shown that the following are formed under the conditions selected: compounds of the dehydroabietane series, stereoisomeric mono- and diepoxides of methyl abietate, and the products of their transformation on the sorbents.The structures and stereochemistries of the compounds isolated have been established with the aid of spectral methods and XSA.
- Kuzakov, E.V.,Shmidt, E.N.,Bagryanskaya, I.Yu.,Gatilov, Yu.V.
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p. 339 - 345
(2007/10/02)
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- REACTION OF METHYL ABIETATE WITH VARIOUS DIENOPHILES AT ZEOLITES
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Two competing processes, the ene reaction and the diene synthesis, occur during the reaction of methyl abietate with acrolein, α-methylacrolein, and maleic anhydride at zeolites, and their ratio depends on the nature of the dienophile.With acrolein the product from the ene reaction is mainly formed.The reaction with α-methylacrolein gives two types of products, i.e., the diastereomeric methyl 7-(2-formylpropyl)abieta-7,13-dien-18-oates and methyl Δ13,14-endo(exo)-15-formyl-15-methyl-13-isopropyl-17-noratis-18-oates.In the reaction with maleic anhydride the Diels-Alder adduct is formed selectively.
- Kuzakov, E. V.,Shmidt, E. N.,Korchagina, D. V.,Bagryanskaya, I. Yu.,Gatilov, Yu. V.,Barkhash, V. A.
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p. 1824 - 1833
(2007/10/02)
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- Conversion of Abietic Acid into Analogues of Ambergris Odorants
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The conversion of methyl abietate (16) into (42) and (43), analogues of the known amber odorants (1) and (2), is reported.
- Cambie, Richard C.,Rutledge, Peter S.,Ryan, Glen R.,Strange, Gary A.,Woodgate, Paul D.
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p. 867 - 881
(2007/10/02)
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- Synthesis of 12-Methoxyabietic Acid Methylester, a Feeding Deterrent of the Larch Sawfly Pristiphora erichsonii (Hartig)
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The diasteromeric methylesters of 12-methoxyabietic acid, an antifeedant for the larch sawfly Pristiphora erichsonii (Hartig) have been synthesised from abietic acid methylester (2).The unknown configuration at C-12 of the natural product has been determined by comparing the spectral and analytical data of the synthesised compounds with data given in the literature for the natural product as being (S). - Keywords: 12-Methoxyabieticacidmethylester; η4--1,2,3,4,4a,4b,5,9,10,10a-Decahydro-1,4a-dimethyl-7-(-1-methylethyl)-1-phenanthrencarboxylic acid methylester>-tricarbonyliron, 1H-, 13C-, 2D-NMR
- Michl, Guenter,Rettenbacher, Christian,Haslinger, Ernst
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p. 833 - 838
(2007/10/02)
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- REACTIONS OF ABIETIC ACID METHYL ESTER WITH m-CHLOROPERBENZOIC ACID
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Abietic acid methyl ester reacts regioselectively with m-chloroperbenzoic acid, in the presence of water to yield a mixture of the two epimeric 13,14-monoepoxides.These epoxides further react affording a mixture of 1,2- and 1,4-unsaturated diols.The overall yield of the reaction is acceptably good (70-80percent).The formation of these and other products are discussed.
- Valverde, Serafin,Lopez, Jose Cristobal,Rabanal, Rosa M.,Escudero, Javier
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p. 573 - 582
(2007/10/02)
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- SYNTHESIS OF (+)-PODOCARP-8(14)-EN-13-ONE AND METHYL-(+)-13-OXO-PODOCARP-8(14)-EN-18-OATE FROM ABIETIC ACID
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An efficient method for the preparation of (+)-podocarp-8(14)-en-13-one 6 and methyl-(+)-13-oxo-podocarp-8(14)-en-18-oate 8 from abietic acid is described.
- Abad, Antonio,Arno, Manuel,Domingo, Luis R.,Zaragoza, Ramon J.
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p. 4937 - 4940
(2007/10/02)
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- Labdane acids and other components of the needles of Pinus pumila
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The terpenoid and aliphatic components of an ethereal extract of the oleoresin of the Japanese stone pine have been investigated.Among them, 33 compounds have been identified, ten of which were isolated in the individual state.The labdane acids of the oleoresin investigated were represented by 19-O-succinylagatholic and 3β-hydroxy-, 3β-acetoxy, and 3-ketoanticopalic acids.
- Raldugin, V. A.,Demenkova, L. I.,Pentegova, V. A.
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p. 192 - 197
(2007/10/02)
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