807630-26-8Relevant articles and documents
A general enantioselective approach to jasmonoid fragrances: Synthesis of (+)-(1R,2S)-methyl dihydrojasmonate and (+)-(1R,2S)-magnolione
Porta, Alessio,Vidari, Giovanni,Zanoni, Giuseppe
, p. 4876 - 4878 (2007/10/03)
Methyl dihydrojasmonate 1 and magnolione 3 are of both academic and industrial interest. In this paper, we describe a flexible, high-yielding route to diastereomerically pure (+)-cis-(1R,2S)-methyl dihydrojasmonate 1 and the first synthesis of (+)-cis-(1R
ENANTIOSELECTIVE PROCESS FOR THE PREPARATION OF METHYL DIHYDROEPIJASMONATE
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Page/Page column 13, (2010/02/09)
An enantioselective process is described for the preparation of methyl dihydroepijasmonate, a compound widely used in cosmetic and perfumes for its fragrant properties.
Easy preparation of methyl 7-epi-jasmonate and four stereoisomers of methyl cucurbate, and assessment of the stereogenic effect of jasmonate on phytohormonal activities
Seto, Hideharu,Nomura, Emi,Fujioka, Shozo,Koshino, Hiroyuki,Suenaga, Toshiro,Yoshida, Shigeo
, p. 361 - 367 (2007/10/03)
To test the stereogenic effect of jasmonate on phytohormonal activities, methyl 7-epi-jasmonate (1b) and four stereoisomers of methyl cucurbate were easily prepared in racemic form: epimerization at the C-7 position of a commercially available methyl jasmonate (2b) with a base and subsequent fractional distillation gave a 46:54 mixture of 1b and 2b, whose reduction gave a mixture of methyl cucurbates (3-6). This synthetic chemistry was supplemented by molecular modeling and an NMR study on 1b and 2b. An assessment of the inhibitory activities of the prepared jasmonates on growth of the second leaf sheath of rice and on seed germination of cress clarified that the cis-configuration of the C-3 and C-7 side chains of jasmonate was an important factor for the high activities. In inhibiting the seed germination of cress, methyl 6-epi-cucurbate (4) exhibited activity that was markedly higher than the other compounds tested, showing that the stereochemistry at C-6 as well as at C-3 and C-7 was strictly recognized by this bioassay.
A convenient synthesis of (-)-methyl epijasmonate
U, Jong Sun,Park, Hyun Seok,Gupta, Sandhya,Cha, Jin Kun
, p. 2931 - 2941 (2007/10/03)
A short, enantioselective synthesis of (-)-methyl epi-jasmonate, ent-1, has been achieved starting from readily available Corey lactone aldehyde 9. The key features include the stereoselective installation of 2,3-cis- disubstituted side-chains by hydrogen
Synthesis of both the enantiomers of methyl epijasmonate
Kitahara, Takeshi,Nishi, Tsunehiro,Mori, Kenji
, p. 6999 - 7006 (2007/10/02)
Both the pure enantiomers of methyl epijasmonate 1 with potato-tuber inducing activity were synthesized stereoselectively starting from 2-oxabicyclo[3.3.0]-oct-6-en-3-one 6 in 20% yield through 11 steps.
Synthesis of Chiral Methyl Cucurbate and Its Analogs
Takehara, Jun,Oritani, Takayuki,Yamashita, Kyohei
, p. 2939 - 2944 (2007/10/02)
Natural (+)-(1R,2S,3S)-methyl cucurbate (1b) and the (-)-δ-lactone of 3-epi-cucurbic acid (16) were synthesized from (+)-(1R,6S,7R)-bicyclonon-3-en-7-ol (5).Asymmetric hydrolysis of the acetate (8) of (+/-)-5 with pancreatin gave optically pure the
An Efficient and Stereocontrolled Synthesis of (+/-)-Methyl Epijasmonate and (+/-)-Cucurbic Acid
Seto, Hideharu,Yoshioka, Hirosuke
, p. 1797 - 1800 (2007/10/02)
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.
Chemistry and Stereochemistry of Iridoids, XIII. - Synthesis of Enantiomerically Pure Methyl (1R,2S,2''Z)-(+)-Jasmonate Starting from Catalpol
Weinges, Klaus,Lernhardt, Ulrich
, p. 751 - 754 (2007/10/02)
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.
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
Montforts, Franz-Peter,Gesing-Zibulak, Ingrid,Grammenos, Wassilios,Schneider, Manfred,Laumen, Kurt
, p. 1852 - 1859 (2007/10/02)
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.
