86891-79-4Relevant academic research and scientific papers
Discovery and synthesis of cyclohexenyl derivatives as modulators of CC chemokine receptor 2 activity
Brown, Gregory D.,Shi, Qing,Delucca, George V.,Batt, Douglas G.,Galella, Michael A.,Cvijic, Mary-Ellen,Liu, Rui-Qin,Qiu, Feng,Zhao, Qihong,Barrish, Joel C.,Carter, Percy H.
, p. 662 - 666 (2016/01/09)
A novel cyclohexenyl series of CCR2 antagonists has been discovered. This series of small, rigid compounds exhibits submicromolar binding affinity for CCR2. Modification of the substituents on the cyclohexene ring led to the identification of potent CCR2 antagonists. Progress from initial lead 5 (IC50 = 700 nM) to (-)-38 (IC50 = 9.0 nM) is discussed.
Increasing the structural span of alkyne metathesis
Persich, Peter,Llaveria, Josep,Lhermet, Rudy,Deharo, Teresa,Stade, Robert,Kondoh, Azusa,Fuerstner, Alois
, p. 13047 - 13058 (2013/10/01)
A new generation of alkyne metathesis catalysts, which are distinguished by high activity and an exquisite functional group tolerance, allows the scope of this transformation to be extended beyond its traditional range. They accept substrates that were previously found problematic or unreactive, such as propargyl alcohol derivatives, electron-deficient and electron-rich acetylenes of various types, and even terminal alkynes. Moreover, post-metathetic transformations other than semi-reduction increase the structural portfolio, as witnessed by the synthesis of a annulated phenol derivative via ring-closing alkyne metathesis (RCAM) followed by a transannular gold-catalyzed Conia-ene reaction. Further examples encompass a post-metathetic transannular ketone-alkyne cyclization with formation of a trisubstituted furan, a ruthenium-catalyzed redox isomerization, and a Meyer-Schuster rearrangement/oxa-Michael cascade. These reaction modes fueled model studies toward salicylate macrolides, furanocembranolides, and the cytotoxic macrolides acutiphycin and enigmazole A; moreover, they served as the key design elements of concise total syntheses of dehydrocurvularin (27) and the antibiotic agent A26771B (36). Ask for more! Many possibilities exist to take advantage of alkyne metathesis. In addition to the approved semi-reduction to stereodefined olefins, it is shown how to convert the products primarily formed into aromatic or heteroaromatic rings, enones, Michael adducts, or β-ketolactones. At the same time, new types of substrates were engaged, including electron-rich, electron-poor, and terminal alkynes, as well as propargyl alcohol derivatives. Copyright
Copper/silver-cocatalyzed conia-ene reaction of linear β-alkynic β-ketoesters
Deng, Chen-Liang,Song, Ren-Jie,Guo, Sheng-Mei,Wang, Zhi-Qiang,Li, Jin-Heng
, p. 5111 - 5114 (2008/03/27)
A novel and general copper/silver catalytic system has been developed for the Conia-ene intramolecular reaction of linear β-alkynic β-ketoesters. In the presence of (CuOTf)2·C 6H6 and AgSbF6 (or AgOAc), a variety of the linear β-alkynic β-ketoesters selectively underwent the Conia-ene intramolecular reaction in moderate to good yields.
Novel Routes to Chiral 2-Alkoxy-5-/6-methoxycarbonylmethylidenepyrrolidines/-piperidines
David, Olivier,Calvet, Sandrine,Chau, Francois,Vanucci-Bacque, Corinne,Fargeau-Bellassoued, Marie-Claude,Lhommet, Gerard
, p. 2888 - 2891 (2007/10/03)
We report the results of a study aimed at the diastereoselective synthesis of chiral 2-alkoxy-5-/6-methoxy carbonylmethylidenepyrrolidines/-piperidines by condensation of chiral amines onto ω-oxo alkynoates and ω-oxo β-keto esters.
Synthetic Studies Aimed at the Dolastanes. An Attempted A + C -> ABC Approach
Belmont, Daniel T.,Paquette, Leo A.
, p. 4102 - 4107 (2007/10/02)
The dolastanes are marine diterpenes whose molecular array of fused 6-7-5 alicyclic rings is distinctive.As part of a program directed toward the synthesis of representatives of these bioactive natural products, the possibility of elaborating their framework by intramolecular cyclization to form the central seven-membered ring has been examined.An expedient two-step route to keto ester 8 was developed.This intermediate proved receptive to copper-promoted conjugate addition of allylmagnesium bromide and lithium.The acetal 21 to be subsequently derived from these adducts could be conveniently crafted into the highly functionalized 2-cyclopentenones 27.Central to the synthetic strategy was the need for intramolecular C-C bond formation within 27.Because we were singularly unsuccessful in achieving the desired end result, this particular approach appears unsuited for gaining access to the dolastanes.
AN ECONOMICAL DIELS-ALDER STRATEGY FOR THE SYNTHESIS OF DAPHNIPHYLLUM ALKALOIDS
Orban, John,Turner, John V.
, p. 2697 - 2700 (2007/10/02)
A convergent and essentially self-consistent strategy, featuring an unusual Diels-Alder reaction has been devised for the stereo-controlled synthesis of a logical tetracyclic precursor 21 to daphniphyllum alkaloids.
