676236-12-7

Upstream product

• 1104389-49-2 C₂₀H₂₆O₃ 
• 676235-98-6 [(1S,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-cyclopenten-1-yl]ethanal 
• 676236-10-5 ether compound 
• 869801-11-6 (1S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-[3',3'-dibromo-2'-propenyl]-2-cyclopentene 
• 676236-09-2 (1S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-(2'-propynyl)-2-cyclopentene 
• 426226-00-8 dimethyl 2-((1R,4S)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-en-1-yl)malonate 
• 660430-04-6 methyl 2-((1S,4S)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-en-1-yl)acetate 
• 115074-49-2 (1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-cyclopentene-1-yl acetate 
• 120052-54-2 (1S,3S)-1-hydroxy-3-(methyl-carboxymethyl)-4-cyclopentene 
• 120052-50-8 2-<(1R,4S)-4-hydroxycyclopent-2-enyl>malonsaeure-dimethylester 
• 676236-11-6 (1S,4R)-4-[7'-(4-methoxybenzyloxy)-2'-heptynyl]-2-cyclopenten-1-ol 

Downstream Products

• 869801-16-1 dienone compound 
• 676236-14-9 dienone compound 
• 676236-13-8 (4S,5S)-5-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-octyl]-4-[7-(4-methoxy-benzyloxy)-hept-2-ynyl]-cyclopent-2-enone 

Relevant academic research and scientific papers

Synthesis of 14,15-epoxyisoprostane A2 phosphorylcholine

The product of the copper-promoted allylic substitution of the 4-hydroxycyclopent-2-enyl ester with TMS-C{triple bond, long}CCH2MgBr was converted to the cyclopentenone with the PMBO(CH2)4CH{double bond, long}CHCH2 side ch

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.