66322-23-4Relevant academic research and scientific papers
Azido-coronatine: A useful platform for "click chemistry"- mediated probe synthesis for bioorganic studies
Okada, Masahiro,Egoshi, Syuusuke,Ueda, Minoru
, p. 2092 - 2095 (2010)
We report on the development of azide-coronatine as a useful platform for azide alkyne cycloaddition ("click chemistry")-mediated synthesis of molecular probes. (p)-Azido-coronatine was synthesized in 10 steps with 11% yield using improved synthesis of coronafacic acid, in which the highly exo-selective Diels-Alder reaction (endo:exo > 1:25) is the key step. Azido coronatine was as effective as the original coronatine in a stomatal opening assay, and was easily modified to a fluorescein isothiocyanate (FITC)-labeled probe with high yield.
A scalable synthesis of (+)-coronafacic acid
Kato, Nobuki,Miyagawa, Saki,Nomoto, Haruna,Nakayama, Misuzu,Iwashita, Makoto,Ueda, Minoru
, p. 423 - 430 (2020/02/11)
A facile, efficient, and scalable synthesis of optically pure coronafacic acid by resolution of racemic coronafacic acid obtained using an improved version of Watson's method has been developed. By optimizing the boron-mediated aldol reaction of Watson, we were able to prepare 2.1 g of racemic coronafacic acid. This was coupled with (S)-4-isopropyl-2-oxazolidinone to give a mixture of diastereomeric coronafacyl oxazolidinones, which were readily separable by silica-gel column chromatography to give 630 mg of optically pure (+)-coronafacic acid.
Total syntheses of coronatines by exo-selective Diels-Alder reaction and their biological activities on stomatal opening
Okada, Masahiro,Ito, Satoko,Matsubara, Akira,Iwakura, Izumi,Egoshi, Syusuke,Ueda, Minoru
experimental part, p. 3065 - 3073 (2011/02/25)
The natural phytotoxin coronatine, which is composed of two individual parts, coronafacic acid and coronamic acid, exhibits various promising biological activities similar to jasmonic acid. Interestingly, coronatine induces stomatal opening involving the swelling of guard cells in which jasmonic acid is not involved as an endogenous regulator. We established syntheses of four stereoisomers of coronatine employing the exo-selective Diels-Alder reaction as a key step. Remarkable differences in stomatal opening activity were observed between enantiomers of coronatine. This result strongly suggests that the stereo structure of coronatine is very important for its stomatal opening activity. In addition, SAR studies suggested that coronatine operates as a molecular mimic of jasmonyl-l-isoleucine in plant guard cells.
Expedient stereoselective synthesis of coronafacic acid through intramolecular Diels-Alder cyclization
Moreau, Benoit,Ginisty, Maryon,Alberico, Dino,Charette, Andre B.
, p. 1235 - 1240 (2007/10/03)
(Chemical Equation Presented) A stereoselective synthesis of coronafacic acid, a natural component of the phytotoxin coronatin, was achieved using an intramolecular Diels-Alder reaction as the key step. The triene precursor bearing a substituted diene and a vinylketone as dienophile was synthesized and then tested in the thermal intramolecular cyclization. We have devised a new strategy to assemble the E,Z-diene through the stereoselective aldol reaction of an ester enolate followed by a stereoselective dehydration. Following the thermal cyclization, the corresponding hydrindanone thereby obtained with the desired relative stereochemistry could easily be converted into the natural product. The synthesis of the coronafacic acid was accomplished in six steps in 29% overall yield.
Total synthesis of coronafacic acid through 6-endo-trig mode intramolecular cyclization of an enone-aldehyde to a hydrindanone using samarium(II) iodide
Sono, Masakazu,Hashimoto, Atsuko,Nakashima, Katsuyuki,Tori, Motoo
, p. 5115 - 5118 (2007/10/03)
Coronafacic acid has been synthesized from a hydrindanone prepared by a 6-endo-trig mode cyclization reaction of the enone-aldehyde with samarium(II) iodide. The stereochemistry of the hydrindanone was controlled by the coordinated samarium species resulting in cis in respect of the hydroxyl group at C-4 and the juncture proton at C-3a. (C) 2000 Elsevier Science Ltd.
Syntheses and Potato Tuber-inducing Activity of Coronafacic Acid Analogues
Toshima, Hiroaki,Nara, Shinji,Ichihara, Akitami,Koda, Yasunori,Kikuta, Yoshio
, p. 681 - 688 (2007/10/03)
Coronafacic acid (1) is an acid component of coronatine, and has been isolated from several pathovars of Pseudomonas syringae. Syntheses of C6-non- and C6-alkyl-substituted analogues of 1 were accomplished via intramolecular 1,6-conjugate addition as the key step. Among them, 1 and four C6-alkyl-substituted analogues exhibited potato tuber-inducing activity, but the C6-non-substituted analogue did not. It was revealed that a certain length of the C6-alkyl group was necessary to exhibit activity.
Asymmetric total syntheses of (+)-coronafacic acid and (+)-coronatine, phytotoxins isolated from Pseudomonas Syringae pathovars
Nara, Shinji,Toshima, Hiroaki,Ichihara, Akitami
, p. 9509 - 9524 (2007/10/03)
Asymmetric total synthesis of (+)-coronafacic acid (2), was accomplished via intramolecular 1, 6-conjugate addition as the key step. The chiral ester (+)-7 was prepared via two approaches: starting from (R)-(+)-4-acetoxy-2- cyclopenten-1-one (12), and using catalytic asymmetric Michael reactions promoted by heterobimetallic BINOL complexes. Coupling between (+)-2 and the protected coronamic acid 8 and subsequent deprotection by hydrogenolysis provided (+)-coronatine (1). This is the first asymmetric total synthesis of(+)-1.
Intramolecular 1,6-conjugate addition approach for construction of the hydrindane framework: Total synthesis of (±)-coronafacic acid
Nara, Shinji,Toshima, Hiroaki,Ichihara, Akitami
, p. 6745 - 6748 (2007/10/03)
A new approach for the construction of the hydrindane framework has been achieved by intramolecular 1,6-conjugate addition under some basic conditions. The precursors, α, β, γ, δ-unsaturated esters (11a-11d) were synthesized from the ester 8 and acrolein derivatives (6a-6d) via aldol condensation. This methodology was applied to the total synthesis of (±)-coronafacic acid and its analogues.
Tandem Wessely oxidation and intramolecular Diels-Alder reactions. IV. The synthesis of (+/-)-coronafacic acid
Yates, Peter,Bhamare, N. K.,Granger, Thierry,Macas, T. S.
, p. 995 - 1001 (2007/10/02)
Ethyl E-5-(4-ethyl-2-hydroxyphenyl)-2-pentenoate (7), prepared in four steps from m-ethylphenol (9), was converted via Wessely oxidation with lead tetraacetate followed by intramolecular Diels-Alder reaction in boiling xylene to ethyl 1-acetyloxy-6-ethyl-2,3,3a,4,5,7a-hexahydro-8-oxo-1,5-methano-1H-indene-anti-4-carboxylate (16).Hydrogenation of 16 followed by mild hydrolysis gave ethyl 6-ethyloctahydro-1-hydroxy-8-oxo-1,5-methano-1H-indene-anti-4-carboxylate (24), which on oxidation with periodate gave 4-(ethoxycarbonyl)-6-ethyloctahydro-1-oxo-1H-indene-5-carboxylic acid (26).Oxidative decarboxylation of this gave a mixture of ethyl 6-ethyl-2,3,3a,6,7,7a-hexahydro-1-oxo-1H-indene-4-carboxylate (31) and ethyl 6-ethyl-2,3,3a,4,7,7a-hexahydro-1-oxo-1H-indene-4-carboxylate (32); the latter was converted to the former by ethanolic sodium ethoxide.Hydrolysis of 31 with hot hydrochloric acid gave (+/-)-coronafacic acid (4).
Stereoselective Route to Functionalized cis-Hydrindanes from Tricyclo2,6>decan-10-ones. A Total Synthesis of (+/-)-Coronafacic Acid
Mehta, Goverdhan,Praveen, Marapaka
, p. 1573 - 1575 (2007/10/02)
A flexible approach to functionalized cis-hydrindanes via Haller-Bauer type cleavage of endo-tricyclo2,6>decan-10-ones is delineated and its efficacy demonstrated through a concise synthesis of (+/-)-coronafacic acid.
