1211-29-6Relevant articles and documents
Lipase-catalyzed preparation of both enantiomers of methyl jasmonate
Kiyota, Hiromasa,Higashi, Emi,Koike, Takanori,Oritani, Takayuki
, p. 1035 - 1038 (2001)
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.
COMPARISONS OF VARIOUS BIOLOGICAL ACTIVITIES OF STEREOISOMERS OF METHYL JASMONATE
Koda, Yasunori,Kikuta, Yoshio,Kitahara, Takeshi,Nishi, Tsunehiro,Mori, Kenji
, p. 1111 - 1114 (1992)
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.
Enantioselective synthesis of (-)-methyl jasmonate and (+)-methyl epijasmonate
Roth, Gerald J.,Kirschbaum, Stephan,Bestmann, Hans Jürgen
, p. 618 - 620 (1997)
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.
Investigation of synthetic lipase and its use in transesterification reactions
Kecili, Rustem,Say, Rdvan,Ers?z, Arzu,Hür, Deniz,Denizli, Adil
body text, p. 1981 - 1984 (2012/06/29)
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.
Stereoselective synthesis of epi-jasmonic acid, tuberonic acid, and 12-oxo-PDA
Nonaka, Hisato,Ogawa, Narihito,Maeda, Noriaki,Wang, Yong-Gang,Kobayashi, Yuichi
experimental part, p. 5212 - 5223 (2010/12/25)
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).
Asymmetric total synthesis of enantiopure (-)-methyl jasmonate via catalytic asymmetric intramolecular cyclopropanation of α-diazo-β-keto sulfone
Takeda, Hiroyuki,Watanabe, Hideaki,Nakada, Masahisa
, p. 8054 - 8063 (2007/10/03)
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.
1,4-Addition of chiral 2-propenylphosphonamide anions to α-substituted cyclopentenones: Use in enantioselective syntheses of methyl dihydrojasmonates and methyl jasmonates
Hailes, Helen C.,Isaac, Ben,Javaid
, p. 7325 - 7328 (2007/10/03)
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.
Synthesis of (±)-methyl epijasmonate and (±)-methyl dihydroepijasmonate by diastereoselective protonation
Krause, Norbert,Ebert, Sophia
, p. 3837 - 3841 (2007/10/03)
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.
Synthesis of methyl epijasmonate and cis-3-(2-oxopropyl)-2-(pent-2Z-enyl)-cyclopentan-1-one
Hailes, Helen C,Isaac, Ben,Hashim Javaid
, p. 10329 - 10333 (2007/10/03)
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.
Occurrence of 11-hydroxyjasmonic acid glucoside in leaflets of potato plants (Solanum tuberosum L.)
Matsuura, Hideyuki,Ohkubo, Yasuhiro,Yoshihara, Teruhiko
, p. 378 - 382 (2007/10/03)
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.
