120330-52-1Relevant academic research and scientific papers
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
CUCURBIC ACID AND ITS 6,7-STEREOISOMERS
Dathe, Wilfried,Schindler, Christiane,Schneider, Gernot,Schmidt, Juergen,Porzel, Andrea,et al.
, p. 1909 - 1914 (2007/10/02)
The derivatives 7-iso-cucurbic acid (7-iso-CA) and 6-epi-7-iso-cucurbic acid (6-epi-7-iso-CA) were prepared from (-)-jasmonic acid (JA) by reduction and cucurbic acid (CA) and 6-epi-cucurbic acid (6-epi--CA) from (+)-7-isojasmonic acid (7-iso-JA).The chromatographic properties (TLC, HPLC, GC) of these derivatives are described and the structures established by physical data. the extracts of different plant materials were analysed with respect to the natural occurence of JA and CA and its 6,7-stereoisomers.JA, 6-epi-CA and 6-epi-7-iso-CA were identified in female flowers of Juglans regia and JA, CA, 6-epi-CA and 6-epi-7-iso-CA in spores of Anemia phyllitidis.JA, CA, 6-epi-CA and 9,10-dihydro-JA were detected in immature caryopses of Secale cereale.In rye JA dominated in young caryopses, while CA level exceeded the amount of JA in the premature fruits.In each tissue 6-epi-CA was found to be a minor component, while CA or 6-epi-7-iso-CA represented the major components; 7-iso-Ca could not be detected.
Stereoselective Synthesis of Methyl Epijasmonate
Kitahara, Takeshi,Warita, Yasuhiro,Abe, Masaki,Seya, Motohide,Takagi, Yoshikazu,Mori, Kenji
, p. 1013 - 1017 (2007/10/02)
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).
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
Crombie, Leslie,Mistry, Kamlesh M.
, p. 1981 - 1991 (2007/10/02)
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.
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.
JASMONIC ACID-LIKE SUBSTANCES FROM THE CULTURE FILTRATE OF BOTRYODIPLODIA THEOBROMAE
Miersch, Otto,Schmidt, Juergen,Sembdner, Guenther,Schreiber, Klaus
, p. 1303 - 1306 (2007/10/02)
Four cyclopentanoidal fatty acids were isolated from the fungus Botryodiplodia theobromae and identified as jasmonic acid-like substances.Their structures are (+)-4,5-didehydro-7-iso-jasmonic acid , ethyl (+)-7-iso-jasmonate , (1R,2S)-(+)-3-oxo-2-(2Z-pentenyl)cyclopent-1-yl-propionic acid and (1S,2S)-3-oxo-2-(2Z-pentenyl)cyclopent-1-yl-butyric acid. - Keywords: Botryodiplodia theobromae; Sphaeropsidaceae; (+)-4,5-didehydro-7-iso-jasmonic acid; ethyl (+)-7-iso-jasmonate; (1R,2S)-(+)-3-oxo-2-(2Z-pentenyl)cyclopent-1-yl-propionic acid; (1S,2S)-(+)-3-oxo-2-(2Z-pentenyl)cyclopent-1-yl-butyric acid.
