- Lipase-catalyzed preparation of both enantiomers of methyl jasmonate
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Preparation of both enantiomeric methyl jasmonates 1 was achieved via lipase-catalyzed resolution of (±)-methyl 7-epicucurbate 3. Lipase P (Amano) provided good selectivity both for acylation of (±)-3 (E = 370) and hydrolysis of the corresponding acetate (E = 41). Resolution of (±)-methyl 6,7-diepicucurbate 2 gave poor results. It was found that the (6R,7S)-configuration was suitable for the selective enzymatic reaction and the C-(3) stereochemistry of the substrate did not influence the enzymatic reaction.
- Kiyota, Hiromasa,Higashi, Emi,Koike, Takanori,Oritani, Takayuki
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Read Online
- COMPARISONS OF VARIOUS BIOLOGICAL ACTIVITIES OF STEREOISOMERS OF METHYL JASMONATE
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Stereoisomers of methyl jasmonate (JA-Me) showed different biological activities in four bioassay systems.Growth of soybean callus was inhibited strongly by (1R,2S)- and (1R,2R)-JA-Me.By contrast, (1S,2R)- and (1S,2S)-JA-Me had very low inhibitory effect on it, suggesting that the activity is dependent largely on the (1R)-configuration.With regard to potato tuber-induction and the senescence-promotion of oat leaves, although the highest activities were found in (1R,2S)-JA-Me, isomers which have the (1S)-configuration showed considerable activities. (1R,2S)- and (1S,2R)-JA-Me equally inhibited straight growth of oat coleoptiles.These results suggest that requirements of the absolute configurations of the two side chains with respect to the plane of the cyclopentanone ring for each activity are different, and that there are different receptors which trigger reactions leading to the individual activity. Key Word Index - Solanum tuberosum; Solanaceae, Glycine max; Leguminosae; Avena sativa; Gramineae, potato tuberization, soybean callus growth; leaf senescence; coleoptile growth; optically pure enantiomers; methyl jasmonate.
- Koda, Yasunori,Kikuta, Yoshio,Kitahara, Takeshi,Nishi, Tsunehiro,Mori, Kenji
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- Enantioselective synthesis of (-)-methyl jasmonate and (+)-methyl epijasmonate
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An efficient and flexible enantioselective synthesis of (-)-methyl jasmonate and (+)-methyl epijasmonate, two important phytohormones, is described. The procedure makes use of a chiral cyclopentanoid building block that can easily be prepared from tartaric acid by phosphorus ylide chemistry.
- Roth, Gerald J.,Kirschbaum, Stephan,Bestmann, Hans Jürgen
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Read Online
- Investigation of synthetic lipase and its use in transesterification reactions
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A novel synthetic polymer selective for p-nitrophenylpalmitate was synthesized by molecular imprinting technique. We have combined the principle of molecular imprinting with the ability of histidine, glutamic acid and serine to form a catalytic cavity that can promote the catalytic degradation of p-nitrophenyl palmitate. For the creation of such catalytic sites we first synthesized appropriate monomers and used p-nitrophenyl palmitate as a template to synthesize the imprinted polymers and the binding characteristics of the polymers were evaluated. The optimum pH was determined by evaluating different pH values and the hydrolytic activity of synthetic lipase was evaluated in the framework of Micheaelis-Menten kinetics. In addition, the values of maximal rate: Vm (0.68 mM/min) and Michaelis-Menten constant, Km (1.4 × 10 -2 mM) were obtained from Lineweaver-Burk plots for the imprinted polymeric catalyst.
- Kecili, Rustem,Say, Rdvan,Ers?z, Arzu,Hür, Deniz,Denizli, Adil
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body text
p. 1981 - 1984
(2012/06/29)
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- Stereoselective synthesis of epi-jasmonic acid, tuberonic acid, and 12-oxo-PDA
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epi-Jasmonic acid (epi-JA) and tuberonic acid (TA) were synthesized from the key aldehyde, all cis-2-(2-hydroxy-5-vinylcyclopentyl)acetaldehyde (14), which was in turn prepared stereoselectively from the (1R)-acetate of 4-cyclopentene-1,3-diol (10) through SN2-type allylic substitution with CH2CHMgBr followed by Mitsunobu inversion, Eschenmoser-Claisen rearrangement, and regioselective Swern oxidation of the corresponding bis-TES ether (13). Wittig reaction of the aldehyde 14 with [Ph3P(CH 2)Me]+Br- followed by oxidation afforded epi-JA (3) stereoselectivity over the trans isomer. Similarly, TA (5) was synthesized. Furthermore, the above findings were applied successfully to improve the total efficiency of the previous synthesis of 12-oxo-PDA (1).
- Nonaka, Hisato,Ogawa, Narihito,Maeda, Noriaki,Wang, Yong-Gang,Kobayashi, Yuichi
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experimental part
p. 5212 - 5223
(2010/12/25)
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- Asymmetric total synthesis of enantiopure (-)-methyl jasmonate via catalytic asymmetric intramolecular cyclopropanation of α-diazo-β-keto sulfone
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A new asymmetric total synthesis of enantiopure (-)-methyl jasmonate is described. This synthesis was accomplished starting from the new enantiopure building block prepared via the catalytic asymmetric intramolecular cyclopropanation (IMCP) of the α-diazo-β-keto 1-naphthyl sulfone, which was devised to give good selectivity both in the IMCP reaction and in the C-alkynylation of the intermediate required for the total synthesis of enantiopure (-)-methyl jasmonate.
- Takeda, Hiroyuki,Watanabe, Hideaki,Nakada, Masahisa
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p. 8054 - 8063
(2007/10/03)
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- Synthesis of (±)-methyl epijasmonate and (±)-methyl dihydroepijasmonate by diastereoselective protonation
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The synthesis of (±)-methyl epijasmonate (1) was carried out by Michael addition of lithium diallylcuprate to enone 3 and diastereoselective enolate protonation with the chelating proton source 2-(methyliminomethyl)phenol (4; 85% ds), followed by ozonolysis, oxidation, esterification, and Lindlar hydrogenation. During the ozonisation, epimerization to the thermodynamically more stable trans-isomer takes place to some extent, so that 1 was isolated with a cis:trans ratio of 72:28. The analogous transformation of enone 7 with lithium diallylcuprate and 2-(methyliminomethyl)phenol (4) furnished ketone 8 with 94% ds; this was then transformed into (±)-methyl dihydroepijasmonate (2) with a cis:trans ratio of 91:9. The olfactory properties of this product are superior to those available from commercial sources.
- Krause, Norbert,Ebert, Sophia
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p. 3837 - 3841
(2007/10/03)
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- Synthesis of methyl epijasmonate and cis-3-(2-oxopropyl)-2-(pent-2Z-enyl)-cyclopentan-1-one
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A novel and efficient synthesis of both (±)-methyl epijasmonate and (±)-cis-3-(2-oxopropyl)-2-(pent-2Z-enyl)-cyclopentan-1-one is described. The key step to establish the cis-stereochemistry on the 5-membered ring is an ionic Diels-Alder reaction, which is high yielding and highly regioselective. Subsequent key steps include oxidative cleavage of the six-membered ring, Wittig coupling and for the synthesis of epijasmonate, the haloform reaction.
- Hailes, Helen C,Isaac, Ben,Hashim Javaid
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p. 10329 - 10333
(2007/10/03)
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- Occurrence of 11-hydroxyjasmonic acid glucoside in leaflets of potato plants (Solanum tuberosum L.)
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In order to examine the occurrence of 11-hydroxyjasmonic acid glucoside in potato plants, a synthesis of 11-hydroxyjasmonic acid was accomplished, and the synthetic compound was employed as a standard for an LC-SIM analysis. The existence of 11-hydroxyjasmonic acid glucoside was proved by the LC-SIM analysis.
- Matsuura, Hideyuki,Ohkubo, Yasuhiro,Yoshihara, Teruhiko
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p. 378 - 382
(2007/10/03)
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- 1,4-Addition of chiral 2-propenylphosphonamide anions to α-substituted cyclopentenones: Use in enantioselective syntheses of methyl dihydrojasmonates and methyl jasmonates
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The addition of chiral 2-propenylphosphonamide anions, generated from the reaction products of (1R,2S)-ephedrine and 2-propene-1-phosphonyl dichloride, to α-substituted cyclopentenones is described. Ozonolysis of the addition products led to the synthesis of both enantiomers of methyl dihydrojasmonate and methyl jasmonate.
- Hailes, Helen C.,Isaac, Ben,Javaid
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p. 7325 - 7328
(2007/10/03)
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- Behaviour of monocomplexed 1,4-diynes in the Khand reaction and use of ethylene equivalent techniques in a convenient route to tritium-labelled methyl jasmonate
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1,2-Complexed hexacarbonyl(hepta-1,4-diyne)dicobalt, obtained from hexacarbonyl(propargyl acetate)dicobalt with tri-1-butynylaluminium, has been converted, by selective Khand annulation of the complexed triple bond with vinyl benzoate, to 2-pent-2-yn-1-ylcyclopent-2-en-1-one. By use of standard procedures this alkynyl cyclopentenone has been transformed into methyl jasmonate, allowing replacement of the final hydrogenation step by tritiation to produce the labelled analogue. Two alternative approaches to the intermediate pentynylcyclopentenone were examined and shown to be unsuccessful.
- Kerr, William J.,McLaughlin, Mark,Pauson, Peter L.
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p. 118 - 124
(2007/10/03)
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- Lavendamycin analogs, quinoline-5,8-diones and methods of using them
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The invention provides novel lavendamycin analogs having the following general formula: and quinoline-5,8-diones having the following formula: Methods of making and using and compositions containing these compounds are also disclosed.
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- A new variant of the Claisen rearrangement from malonate-derived allylic trimethylsilyl ketene acetals: Efficient, highly enantio- and diastereoselective syntheses of (+)-methyl dihydroepijasmonate and (+)-methyl epijasmonate
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Complete chirality transfer occurs in the smooth Claisen rearrangement of the trimethylsilyl (TMS) ketene acetals, which were prepared from allylic malonates (R)-1 (R = pentyl, 2-(Z)-pentenyl). These are in turn accessible by enantioselective reduction/esterification or by enzymatic kinetic resolution. The cis configuration in (+)-3 was achieved by highly syn-selective epoxidation of (+)-2, followed by suprafacial 1,2-H migration.
- Fehr, Charles,Galindo, Jose
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p. 569 - 573
(2007/10/03)
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- Quinoline-5,8-diones and methods of using them
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The invention provides quinoline-5,8-diones having the following formula: STR1 wherein X, Z and R1 through R3 are defined in the specification, and salts of these quinolinediones. The invention also provides a method of making the quinolinediones. The quinolinediones have antitumor activity.
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- Stereochemical Control over Three Contiguous Stereogenic Centers in the Intramolecular Ene Reaction of Activated 1,6-Dienes. Application to the Synthesis of (±)-Methyl Cucurbate and (±)-Methyl Epijasmonate
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The influence of a protected alcohol group adjacent to the ene or enophile component on diastereoselectivity in both thermal and Lewis acid-catalyzed 5-(3,4) ene reactions of a series of 1,6-dienes 1-7 has been studied. The results indicate that its effect can be considerable, and in one example, with a gem-dimethyl group on the connecting chain and a large silyl protecting group on the hydroxyl, the diastereocontrol was almost perfect, with three stereogenic centers and one double bond geometry set up in one step, e.g., 4 → 10. This new finding was exploited in a synthesis of epijasmonoid natural products, (±)-methyl cucurbate (19) and (±)-methyl epijasmonate (18) starting from aldehyde 24, where the key step was a highly diastereocontrolled 5-(3,4) ene cyclization 23 → 22. 1 Indian Institute of Technology 2 BARC.
- Sarkar, Tarun K.,Ghorai, Binay K.,Nandy, Sandip K.,Mukherjee, Bireswar,Banerji, Asoke
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p. 6006 - 6011
(2007/10/03)
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- Di-lysoganglioside derivatives
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N-acyl-N,N''-di-lysogangliosides, N''-acyl-N,N''-di-lysogangliosides and N,N''-diacyl-N,N''-di-lysogangliosides, wherein the acyl groups are derived from an aliphatic acid having from 1 to 24 carbon atoms, substituted by one or more polar groups are disclosed. The acyl-di-lysogangliosides of the invention exhibit an inhibiting action on protein kinase C activation and, thus, can be utilized in therapies for various pathologies of the nervous system. Pharmaceutical compositions and therapeutic utilities for the lysoganglioside derivatives are also disclosed.
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- (-)-Methyl cucurbate and (-)-methyl jasmonate by kinetic resolution
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The kinetic resolution of a malonate-substituted cyclopentenone gave rise to the formation of an enantiopure Diels-Alder adduct which was converted into methyl dehydrocucurbate 2 by diastereoselective alkylation with (Z)-1-bromo-2-pentene and subsequent borohydride reduction. Selective hydrogenation of 2 with a palladium/calcium carbonate catalyst proved to be a reliable route to (-)-methyl cucurbate (1) the oxidation of which with pyridinium chlorochromate and subsequent treatment with acid afforded (-)-methyl jasmonate (9). VCH Verlagsgesellschaft mbH, 1996.
- Borm, Claudia,Winterfeldt, Ekkehard
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p. 1209 - 1212
(2007/10/03)
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- Vitamin-B12-catalyzed C,C-bond formation: Synthesis of jasmonates via sequential radical reaction
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The Cbl-catalyzed electroreduction of 3-(2'-bromo-1'-ethoxyethoxy)cyclopenten (1a) in presence of 1-cyanovinyl-acetate (8) gave, in a sequential radical reaction (5-exo-trig-cyclization of 1a following by addition to 8), 1-cyano-2-(2'-ethoxy-hexahydro-2'H-cyclopenta[b]furan-4'-yl)ethyl acetate (10a). This intermediate was transformed to methyl jasmonate (7; four steps) and epituberolide (9; three steps) in 20 and 31% yield, respectively, from cyclopent-2-en-1-ol.
- Busato,Scheffold
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- Intramolecular Alder ene approach to stereochemical control over three contiguous stereogenic centres: Synthesis of (±)-methyl cucurbate and (±)-methyl epijasmonate
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The total synthesis of epijasmonoids, (±)-methyl cucurbate and (±)-methyl epijasmonate is described starting from aldehyde 14, where the key step is a highly stereocontrolled 5-(3,4) ene cyclization 17→18.
- Sarkar, Tarun K.,Ghorai, Binay K.,Banerji, Asoke
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p. 6907 - 6908
(2007/10/02)
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- Compounds of N-benzoylpyroline
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Compounds of the general formula (I): STR1 where A, R1, R2, R3, R4, R5 and R6 are defined in the description. Medicinal products.
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- Substituted and unsubstituted alkyl cyclohexylmethyl and cyclohexenylmethyl carbonates and perfumery uses thereof
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Described are alkyl cyclohexylmethyl and cyclohexenylmethyl carbonates defined according to the generic structure: STR1 wherein R1 is methyl or ethyl; R2, R3, R4 and R6 represents hydrogen or methyl; R5 represents hydrogen, methyl or methylene; and R7 represents hydrogen or C1 -C4 straight chain lower alkyl or isopropyl or R7 is no moiety; each of the dashed lines represents a carbon-carbon single bond or a carbon-carbon double bond; the wavy line represents a carbon-carbon single bond or no bond; with the provisos that: (a) at least three of the dashed lines each represents a carbon-carbon single bond; (b) when R7 is no moiety, the dashed line at the "1-6" position is a carbon-carbon double bond; (c) when the wavy line is a carbon-carbon single bond then R5 is methylene and the carbon-carbon bond at the "4-5" position and at the "5-6" position is a carbon-carbon single bond; and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles, such as solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles, hair sprays, shampoos, bath oils and perfumed polymers.
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- Di-lysogangliosides derivatives
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N-acyl-N,N?-di-lysogangliosides, N?-acyl-N,N?-di--lysogangliosides and N,N?-diacyl-N,N?-di--lysogangliosides, wherein the acyl groups are derived from an aliphatic acid having from 1 to 24 carbon atoms, substituted by one or more polar groups. The acyl-di--lysogangliosides of the invention exhibit an inhibiting action on protein kinase C activation and, thus, can be utilized in therapies for various pathologies of the nervous system. Pharmaceutical compositions and therapeutic utilities for the lysoganglioside derivatives are also disclosed.
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- Stereoselective Synthesis of Methyl Epijasmonate
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Methyl epijasmonate (1) was stereoselectively synthesized from 3-hydroxymethylcyclopentanone (7).The intramolecular alkylation of bromoketone (8) or (9) was the key step to exclusively afford thermodynamically more stable oxahydrindanone (10) or (11).Synthesis was achieved in a 6percent overall yield in 12 steps from (7).
- Kitahara, Takeshi,Warita, Yasuhiro,Abe, Masaki,Seya, Motohide,Takagi, Yoshikazu,Mori, Kenji
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p. 1013 - 1017
(2007/10/02)
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- Synthesis of 12-Oxophytodienoic Acid (12-OxoPDA) and the Compounds of its Enzymic Degradation Cascade in Plants, OPC-8:0, -6:0, -4:0 and -2:0 (epi-Jasmonic Acid), as their Methyl Esters
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The synthesis of 12-Oxophytodienoic acid, and the compounds of its enzymatic degradation sequence, OPC-8:0, -6:0, -4:0 and -2:0, important plant metabolites derived from linolenic acid, is reported.The syntheses use the known cyclopent-3-ene-1,2-diacetic acid as an early intermediate, and this is derived from the Cope rearrangement of 5-vinyltrinorborn-2-ene via bicyclonona-3,7-diene.Iodolactonisation and tributyltin hydride reduction provides the key intermediate (3-oxo-2-oxabicyclooctan-6-yl)acetic acid for the OPC series, whilstphenylselenolactonisation and elimination provides the necessary unsaturated lactone (7-oxo-8-oxabicyclooct-2-en-4-yl)acetic acid for 12-oxoPDA.Members of the OPC-series were made by chain extending the saturated oxabicyclooctane acid: that for the OPC-4:0 involved double Arndt-Eistert reaction, whilst the intermediates for OPC-6:0 and -8:0 were made by Kolbe anodic crossed coupling.The lactones were than converted via their lactols, Wittig reaction, esterfication and oxidation, into the compounds of the OPC ester series, including OPC-2:0 (methyl epi-jasmonate).The unsaturate lactone 8-(7-oxo-8-oxabicyclooct-2-en-4-yl)octanoic acid required for 12-oxoPDA synthesis could also be prepared by anodic synthesis either from (7-oxo-8-oxa-bicyclooct-2-en-4-yl)acetic acid, or from its 2-phenylseleno-2,3-dihydro precursor as elimination occurred concomitantly during the reaction.Since yields were low, the unsaturated acid lactone was converted into its lactol and the (Z)-pent-2-enyl side-chain was inserted first.After TBDMS blocking of the cyclopentene hydroxy group, the side-chain was elaborated to give5-(pent-2-enyl)cyclopent-2-enylacetaldehyde and chain extension carried out by a Grignard-demesylation procedure.Sequential desilylation and depyranylation, followed by oxidation of the diol, gave 12-oxoPDA, isolated as its methyl ester.
- Crombie, Leslie,Mistry, Kamlesh M.
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p. 1981 - 1991
(2007/10/02)
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- An Efficient and Stereocontrolled Synthesis of (+/-)-Methyl Epijasmonate and (+/-)-Cucurbic Acid
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The total synthesis of epijasmonoids, (+/-)-methyl epijasmonate and (+/-)-cucurbic acid, starting from norbornene was described, where a key intermediate, 5β-hydroxy-2β-methoxycarbonylmethylcyclopentane 1β-acetic acid γ-lactone was efficiently prepared via a highly regioselective Baeyer-Villiger oxidation of 7-syn-substituted norbornanone based on remote substituent control.
- Seto, Hideharu,Yoshioka, Hirosuke
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p. 1797 - 1800
(2007/10/02)
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- Chemistry and Stereochemistry of Iridoids, XIII. - Synthesis of Enantiomerically Pure Methyl (1R,2S,2''Z)-(+)-Jasmonate Starting from Catalpol
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Enantiomerically pure methyl (1R,2S,2''Z)(+)-jasmonate (2), which was recognized as a component of the fragrance of the jasmine flower oil, was synthesized starting from catalpol (3). 2 is easily epimerized to 1.Thus, it is necessary to use very mild conditions in the course of the synthesis and purification.These results raise the question whether 2 exists as a natural product in the flower of jasmine and 1 arises during the isolation.
- Weinges, Klaus,Lernhardt, Ulrich
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p. 751 - 754
(2007/10/02)
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- Process for the preparation of cyclopentanoids and novel intermediates produced thereby
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Cyclopentanoids (I) of the formula: STR1 including stereoisomers are described along with a process for the preparation of I. In particular the preparation of prostanoids of the formula: STR2 wherein R1 is a alkyl group containing 1 to 8 carbon atoms and R2 CO2 R3 is an alkenyl ester group, R2 contains 2 to 6 carbon atoms and R3 is a lower alkyl group containing 1 to 6 carbon atoms is described. A particular prostaglandin prepared by the process is PGE2. The prostanoids have been demonstrated to have pharmacological activity in animals and humans. Novel intermediates of (I) are also described.
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- Methyl-jasmonat: Ein kurzer Weg zum Naturstoff und seinem unnatuerlichen Enantiomer via Palladium(0)-induzierte, enantiodivergente Alkylierung von Cyclopent-2-en-1,3-diol-Derivaten
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Palladium-catalyzed alkylation of cyclopent-2-ene-1,2-diol derivatives like 2 is a useful method for enantiodivergent functionalization, resulting both enantiomeric series of chiral building blocks.The chiral building blocks 3 and 13 can be transformed to methyl-jasmonate (1) and its unnatural enantiomer ent-1, recent statement that 1 has no odour at all and that "methyl-jasmonate's" fragrance is actually due to its cis-isomer ent-11 has been confirmed also for the enantiomeric series.
- Montforts, Franz-Peter,Gesing-Zibulak, Ingrid,Grammenos, Wassilios,Schneider, Manfred,Laumen, Kurt
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p. 1852 - 1859
(2007/10/02)
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- INTRAMOLECULAR ENE APPROACH TO STEREOCONTROLLED SYNTHESIS OF CYCLOPENTANOIDS
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A new and stereoselective approach to cyclopentanoid synthesis is described.The key step is the thermal intramolecular ene reaction of 4-carboxymethyl-7-benzyloxy-5-heptanal, prepared by the Claisen rearrangement, to afford 2,3-disubstituted cyclopentanol derivative in a highly stereoselective fashion.
- Takahashi, Kazuhiko,Sato, Hisao,Mikami, Koichi,Nakai, Takeshi
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p. 247 - 250
(2007/10/02)
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- Synthesis of compounds of the 12-oxophytodienoic acid cascade: OPCs-8:0, 6:0, 4:0, and 2:0 (epi-jasmonic acid)
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The β-oxidation compounds of the cis series OPC-8:0, 6:0, 4:0, and 2:0 (epi-jasmonic acid), formed metabolically from dihydro-12-oxophytodienoic acid, are synthesised as their methyl esters; plant regulating functions are associated with the acids of this series.
- Crombie, Leslie,Mistry, Kamlesh M.
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p. 539 - 540
(2007/10/02)
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- Synthesis of (+/-)-Methyl Epijasmonate and (+/-)-Methyl Cucurbate
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A novel synthesis of (+/-)-methyl epijasomonate (2) and the first synthesis of (+/-)-methyl cucurbate (4) were achieved startig from 2-allocyclohexane-1,3-dione (8).The synthetic epimer 2 had a stronger jasmin flavor than the trans-isomer 1 with 95percent purity.
- Kitahara, Takeshi,Miura, Katsutoshi,Warita, Yasuhiro,Takagi, Yoshikazu,Mori, Kenji
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p. 1129 - 1134
(2007/10/02)
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- Chemistry and Stereochemistry of Iridoids, IX.- EPC Synthesis of (1R,2R,2''Z)-(-)-Methyl Jasmonate from Catalpol - Crystal and Molecular Structure of Methyl Dehydrojasmonate Semicarbazone
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Catalpol is converted into the enantiomerically pure (1R,2R,2''Z)-(-)-methyl jasmonate (1) by a 16-step synthesis (yield about 7percent).The R-configuration at C-1 of 1 results from the synthesis.The complete stereochemistry of 1 is confirmed by the X-ray analysis of methyl dehydrojasmonate semicarbazone (semicarbazone of 12).
- Weinges, Klaus,Gethoeffer, Hanspeter,Huber-Patz, Ursula,Rodewald, Hans,Irngartinger, Hermann
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p. 361 - 366
(2007/10/02)
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- (+)-7-ISO-JASMONIC ACID AND RELATED COMPOUNDS FROM BOTRYODIPLODIA THEOBROMAE
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Metabolites produced by Botryodiplodia theobromae (synonym Lasiodiplodia theobromae) possessing plant growth regulating activities were shown to be 7-epimer of jasmonic acid and its derivatives. - Key Word Index: Botryodiplodia theobromae; Sphaeropsidaceae; (+)-7-iso-jasmonic acid; (+)-9,10-dihydro-7-iso-jasmonic acid; (+)-11,12-didehydro-7-iso-jasmonic acid; (+)-cucurbic acid.
- Miersch, Otto,Preiss, Alfred,Sembdner, Guenther,Schreiber, Klaus
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p. 1037 - 1040
(2007/10/02)
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- AN EFFICIENT SYNTHETIC METHOD OF METHYL (+/-)-JASMONATE
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An efficient synthetic method of methyl (+/-)-jasmonate is described. 2-Pentynyl-2-cyclopentenone, the key intermediate in this route, was synthesized by applying the palladium-catalyzed enone formation from allyl β-keto carboxylate as a key reaction.
- Kataoka, Hideaki,Yamada, Toshiro,Goto, Kuniaki,Tsuji, Jiro
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p. 4107 - 4112
(2007/10/02)
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- Process for preparing alkyl substituted para-carboalkoxy cyclohexanones
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Described are para-carboalkoxy cyclohexanones defined according to the structure: STR1 wherein R1 represents hydrogen or C1 -C7 alkyl and R2 represents methyl or ethyl and uses thereof in augmenting or enhancing the aroma of consumable materials including foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, cosmetic compositions, fabric softener compositions, fabric softener articles, hair preparations and perfumed polymers. The compounds defined according to the structure: STR2 wherein R1 ' represents C4 -C7 alkyl and R2 represents methyl or ethyl are novel compounds.
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- A MILD AND STEREOSPECIFIC CONVERSION OF VICINAL DIOLS INTO OLEFINS VIA 2-METHOXY-1,3-DIOXOLANE DERIVATIVES
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An efficient and practical method for the stereospecific synthesis of olefins from vicinal diols via the corresponding 2-methoxy-1,3-dioxolanes is reported.
- Ando, Masayoshi,Ohhara, Hiroshi,Takase, Kahei
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p. 879 - 882
(2007/10/02)
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- Optical Resolution of Methyl Jasmonate and Methyl Epijasmonate
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Optical isomers of methyl jasmonate were resolved from a commercial mixture via the formation of bornyl jasmonate diastereoisomers.The symmetry and magnitude of the optical rotation spectra, and the observation that only one isomer, (+)-methyl epijasmonate had the characteristic methyl jasmonate odor indicated that these preparations were optically pure.
- Nishida, Ritsuo,Acree, Terry E.,Fukami, Hiroshi
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p. 769 - 772
(2007/10/02)
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- PALLADIUM-CATALYZED ALLYLATION OF LITHIUM 3-ALKENYL-1-CYCLOPENTENOLATES-TRIETHYLBORANE AND ITS APPLICATION TO A SELECTIVE SYNTHESIS OF METHYL (Z)-JASMONATE
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A Pd-catalyzed allylation of 3-substituted 1-cyclopentenolates with readily obtainable and storable γ-monosubstituted (Z)-allylic acetates in a 1:1 ratio in the presence of 2 mol percent of Pd(PPh3)4 featuring high yields and high stereo- and regioselectivities has been developed and applied to the synthesis of methyl (Z)-jasmonate.
- Luo, Fen-Tair,Negishi, Ei-ichi
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p. 2177 - 2180
(2007/10/02)
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- CONJUGATE ADDITION OF LITHIOTRIMETHYLSILYLACETATE. A SIMPLE SYNTHESIS OF METHYL JASMONATE VIA VICINAL DOUBLE ALKYLATION
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Exceptional conjugate addition of methyl lithiotrimethylsilylacetate to cyclopentenone has been found and can be applied to a convenient synthesis of methyl jasmonate by sequential vicinal double alkylation via succesful stannyl enolate trapping.
- Nishiyama, Hisao,Sakuta, Koji,Itoh, Kenji
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p. 2487 - 2488
(2007/10/02)
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- 211. Michael Addition of Lithio-α-(methyldiphenylsilyl)acetate to Cyclopentenone: A Direct Synthesis of (+/-)-Methyl Jasmonate
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Aprotic 1,4-addition of a lithiated α-(methyldiphenylsilyl)acetate to cyclopentenone and in situ enolate alkylation provides a direct synthesis of (+/-)-methyl jasmonate (Scheme 3).
- Oppolzer, Wolfgang,Guo, Modao,Baetting, Kurt
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p. 2140 - 2144
(2007/10/02)
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- An Efficient Synthesis of Methyl Jasmonate and Methyl Dihydrojasmonate
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A simple and an efficient synthesis of methyl jasmonate (1) and methyl dihydrojasmonate (5) is described.Starting from alkyl acetoacetate or acetonedicarboxylate, 1 and 5 were obtained in only a few steps via intramolecular Michael addition.
- Kitahara, Takeshi,Mori, Kenji,Matsui, Masanao,Iwamoto, Minoru,Takagi, Yoshikazu,Warita, Yasuhiro
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p. 1369 - 1376
(2007/10/02)
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- An Efficient Synthesis of Methyl dl-cis-Jasmonate
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An efficient synthesis of methyl dl-cis-jasmonate is described, starting from the previously described 2-(methoxycarbonyl)-3-cyclopentanone (3), itself easily prepared from succinyl chloride and methyl potassium malonate.Alkylation of 3 with 1-bromo-2-pentyne followed by selective removal of the 2-carbomethoxy group gave dehydrojasmonic acid.On esterification and reduction (H2/Pd/C/pyridine) of the triple bond to the cis olefin, dehydrojasmonic acid afforded methyl dl-cis-jasmonate in 40percent overall yield from succinyl chloride.
- Johnson, Francis,Paul, Kenneth G.,Favara, D.
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p. 4254 - 4255
(2007/10/02)
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- Resolution of (+/-)-Methyl Jasmonate by High Performance Liquid Chromatography and the Inhibitory Effect of (+)-Enantiomer on the Growth of Rice Seedlings
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(+/-)-Methyl jasmonate (JA-Me) was resolved by preparative high performance liquid chromatography of its diastereomeric ketal with (-)-2,3-butanediol to give optically pure (+)-JA-Me, while the optical purity of the (-)-form obtained by the resolution was 81.2-81.9percent.The inhibitory activity of (+)-JA-Me on the growth of rice seedlings was found to be lower than that of the naturally occurring (-)-form, the (+)-form being still fairly potent.
- Yamane, Hisakazu,Takahashi, Nobutaka,Ueda, Jun-ichi,Kato, Jiro
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p. 1709 - 1712
(2007/10/02)
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- An Efficient Total Synthesis of (+/-)-Methyl Jasmonate
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A short synthesis of Methyl dl-Jasmonate from bicyclo nona-3,8-diene is described.
- Stevenes, Robert V.,Hrib, Nick
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p. 4791 - 4794
(2007/10/02)
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- Convenient Synthesis of Jasmonoid Compounds from γ-(Trimethylsiloxy)butyronitrile
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1,4-Dioxygenated compounds 4 are constructed by the addition of a Grignard reagent to γ-(trimethylsiloxy)nitriles 1,2, and 3 and subsequent hydrolysis.Oxidation of 4 with pyridinium chlorochromate or Jones reagent yields compounds 5 which are used to produce cyclopentenones 6.Methyl jasmonate and methyl dihydrojasmonate are made by the conjugate addition of silylated ketene acetal 9 to 6a and 6b, respectively, and subsequent protodesilylation. γ-Jasmolactone is also derived from 4a by oxidation with pyridinium dichromate in DMF followed by reduction with NaBH4 in ethanol.
- Matsuda, Isamu,Murata, Shizuaki,Izumi, Yusuke
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p. 237 - 240
(2007/10/02)
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- Antibiotic A-26771 factor
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Antibiotic mixture A-26771, comprising microbiologically active factors A, B and C, produced by fermentation of Penicillium turbatum Westling NRRL 5630, and isolation and separation of the individual factors thereof by extraction, chromatography and crystallization. The A-26771 mixture and factors A, B and C thereof have antifungal and broadspectrum antibacterial activity; factors A and C also have antiviral activity.
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