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15-Deoxy-delta12,14-Prostaglandin J2 is an endogenous PPARγ ligand and TRPA1 agonist.

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• 869801-20-7 (Z)-7-((S,E)-5-((E)-oct-2-en-1-ylidene)-4-oxocyclopent-2-en-1-yl)hept-5-enal 
• 60410-16-4 (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate 
• 120052-50-8 2-<(1R,4S)-4-hydroxycyclopent-2-enyl>malonsaeure-dimethylester 
• 120052-54-2 (1S,3S)-1-hydroxy-3-(methyl-carboxymethyl)-4-cyclopentene 
• 115074-49-2 (1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-cyclopentene-1-yl acetate 
• 660430-04-6 methyl 2-((1S,4S)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-en-1-yl)acetate 
• 426226-00-8 dimethyl 2-((1R,4S)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-en-1-yl)malonate 
• 676235-98-6 [(1S,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-cyclopenten-1-yl]ethanal 
• 676236-01-4 (4R)-4-{(2Z)-7-[(4-methoxybenzyl)oxy]hept-2-en-1-yl}cyclopent-2-en-1-one 
• 869801-10-5 (1S,4R,2'Z)-4-[7'-(4-methoxybenzyloxy)-2'-heptenyl]-2-cyclopenten-1-ol 
• 869801-19-4 (S,E)-4-((Z)-7-hydroxyhept-2-en-1-yl)-5-((E)-oct-2-en-1-ylidene)cyclopent-2-enone 
• 676236-00-3 (1S,4R,2'Z)-1-[(tert-butyldimethylsilyl)oxy]-4-[7'-(4-methoxybenzyloxy)-2'-heptenyl]-2-cyclopentene 
• 869801-12-7 (S,E)-4-((Z)-7-((4-methoxybenzyl)oxy)hept-2-en-1-yl)-5-((E)-oct-2-en-1-ylidene)cyclopent-2-enone 
• 1253966-22-1 C₂₁H₃₀O₃ 

Relevant academic research and scientific papers

Nonenzymatic free radical-catalyzed generation of 15-deoxy-Δ 12,14- Prostaglandin J2-like compounds (deoxy-J 2-isoprostanes) in vivo1

15-Deoxy-δ12,14 -prostaglandin J2(15-d-PGJ 2) is a reactive cyclopentenone eicosanoid generated from the dehydration of cyclooxygenase-derived prostaglandin D2(PGD 2). This compound possesses an α , β -unsaturated carbonyl moiety that can readily adduct thiol-containing biomolecules such as glutathione and cysteine residues of proteins via the Michael addition. Due to its reactivity, 15-d-PGJ2is thought to modulate infl ammatory and apoptotic processes and is believed to be an endogenous ligand for peroxisome proliferator-activated receptor- γ . However, the extent to which 15-d-PGJ2is formed in vivo and the mechanisms that regulate its formation are unknown. Previously, we have reported the formation of PGD 2and PGJ2-like compounds, termed D2/J 2-isoprostanes (D2/J2-IsoPs), produced in vivo by the free radical-catalyzed peroxidation of arachidonic acid (AA). Based on these fi ndings, we investigated whether 15-d-PGJ2-like compounds are also formed via this nonenzymatic pathway. Here we report the generation of novel 15-d-PGJ2-like compounds, termed deoxy-J2- isoprostanes (deoxy-J2-IsoPs), in vivo, via the nonenzymatic peroxidation of AA. Levels of deoxy-J2-IsoPs increased 12-fold (6.4 ± 1.1 ng/g liver) in rats after oxidant insult by CCl 4 treatment, compared with basal levels (0.55 ± 0.21 ng/g liver). These compounds may have important bioactivities in vivo under conditions associated with oxidant stress. -Hardy, K. D., B. E. Cox, G. L. Milne, H. Yin, and L. Jackson Roberts II. Nonenzymatic free radical-catalyzed generation of 15-deoxy- δ12,14- Prostaglandin J2-like compounds (deoxy-J2-isoprostanes) in vivo. by the American Society for Biochemistry and Molecular Biology, Inc.

Total synthesis of prostaglandin J natural products and their intermediates

The present disclosure is directed to methods of preparing prostaglandin J natural products by stereoretentive metatheses reactions and intermediates used in the synthesis of these natural products, including the use of intermediates of Formula (I-A), where R1 is defined in the specification

Concise Syntheses of ?"12-Prostaglandin J Natural Products via Stereoretentive Metathesis

δ12-Prostaglandin J family is recently discovered and has potent anticancer activity. Concise syntheses of four δ12-prostaglandin J natural products (7-8 steps in the longest linear sequences) are reported, enabled by convergent stereoretentive cross-metathesis. Exceptional control of alkene geometry was achieved through stereoretention.

TOTAL SYNTHESIS OF PROSTAGLANDIN J NATURAL PRODUCTS BY STEREORETENTIVE METATHESIS

This invention relates generally to the synthesis of Δ12-Prostaglandin J product using stereoretentive ruthenium olefin metathesis catalysts supported by dithiolate ligands. Δ12- Prostaglandin J products were generated with excellent selectivity (>99% Z) and in moderate to high/good yields (47% to 80% yield; 58% to 80% yield).

Identification and Structural Analysis of New Nrf2 Activators by Mechanism-Based Chemical Transformation of 15-Deoxy-Δ12, 14-PGJ2

Mechanism-based chemical transformation of 15-deoxy-Δ12, 14-PGJ2 (15d-PGJ2) resulted in a series of new NF-E2-related factor-2 (Nrf2) activators and detailed elucidation of the function of each electrophilic binding site. In addition, HO-1 expression resulting from Nrf2 activation through enhanced dissociation of the Keap1–Nrf2 complex by the new activators was proved.

Total Synthesis of Prostaglandin 15d-PGJ2 and Investigation of its Effect on the Secretion of IL-6 and IL-12

An efficient synthesis of 15-deoxy-Δ12,14-prostaglandin J2 (15d-PGJ2, 1) is reported. The route described allows for diversification of the parent structure to prepare seven analogues of 1 in which the positioning of electrophilic sites is varied. These analogues were tested in SAR studies for their ability to reduce the secretion of proinflammatory cytokines. It was shown that the endocyclic enone is crucial for the bioactivity investigated and that the conjugated ω-side chain serves in a reinforcing manner.

Concise and enantioselective total synthesis of 15-deoxy-Δ 12,14-prostaglandin J2

The concise and enantioselective synthesis of 15-deoxy-Δ 12,14-prostaglandin J2 (15d-PGJ2) has been accomplished in 11 steps from a known alcohol. The key step of the synthesis involves an asymmetric Rh-catalyzed cycloisomerization of ene-ynone, followed by an olefin isomerization.

Highly efficient total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and their analogues

Palladium-catalyzed reaction of TBS ether of 4-cyclopentene-1,3-diol monoacetate (>95% ee) with an anion derived from methyl malonate and a base such as t-BuOK and LDA proceeded highly efficiently and reproducibly. The product obtained in >90% isolated yield was transformed in five steps into the key cyclopentenone possessing the α-chain at the γ position. Aldol reaction of this enone with the ω-chain aldehyde afforded the aldol adduct, and exposure of the derived mesylate to Al2O3 furnished the cross-conjugated dienone of the full structure. Finally, functional group manipulation furnished Δ12-PGJ2 efficiently. Similarly, 15-deoxy-Δ12,14-PGJ2, 5,6-acetylene analogues, and a 5,6-dihydro analogue were synthesized.

METHOD FOR PRODUCING PROSTAGLANDIN DERIVATIVE, PROSTAGLANDIN DERIVATIVE, INTERMEDIATE COMPOUND THEREFOR AND METHOD FOR PRODUCING THE SAME

PROBLEM TO BE SOLVED: To provide a method for producing a prostaglandin derivative, the prostaglandin derivative and an intermediate compound therefor, especially a method for producing a δ-12-prostaglandin J2 derivative using a new method for chemical synthesis through the intermediate compound. SOLUTION: The method for production is a method for producing the prostaglandin derivative using (1R,3R)-4-cyclopentene-1,3-diol 3-acetate (carboxylate) as a starting material. The method is composed of (A) an α-side chain introduction step of providing a malonic acid ester addition compound at the 3-position of the (1R,3R)-4-cyclopentene-1,3-diol, (B) an α-side chain extension step of affording a (1R,3R)-4-cyclopenten-1-one compound having the α-side chain of the prostaglandin derivative at the 3-position and (C) a prostaglandin derivative synthesizing step of conversion into the prostaglandin derivative.

Total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and related compounds

A key cyclopentenone possessing the α-chain was synthesized from TBS ether of 4-cyclopentene-1,3-diol monoacetate, and submitted to aldol reaction at the α′-position with the ω-chain aldehydes followed by dehydration to produce the title compounds. In a similar manner, 5-dehydro compounds (acetylene analogues) were synthesized successfully. In addition, palladium-catalyzed reaction of 4-cyclopentene-1,3-diol monoacetate with methyl malonate, the first step of the synthesis, was improved to afford the product in high yield by using t-BuOK or LDA in place of NaH.