125702-14-9Relevant articles and documents
Modular 1,1′-Ferrocenediyl-cored P-Stereogenic Diphosphines: ′′JDayPhos′′ Series and its Use in Rhodium(I)-Catalyzed Hydrogenation
Poklukar, Ga?per,Stephan, Michel,Mohar, Barbara
supporting information, p. 2566 - 2570 (2018/05/16)
A novel ferrocene-based P-stereogenic diphospine ligand series dubbed JDayPhos was developed, which rhodium(I) complexes of some of its members exhibited excellent enantioselectivity (up to >99% ee) and high activity in asymmetric hydrogenation of β-unsubstituted or -substituted itaconates and α-methylene-γ-oxo-carboxylates. (Figure presented.).
NOVEL COMPOUNDS AND THEIR USE IN THERAPY
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Page/Page column 110-111, (2013/06/27)
The invention provides compounds which inhibit N-myristoyltransferase and are selective for protozoal N-myristoyltransferase and, consequently suitable to treat microbial infections, including viral and fungal infections, and protozoan infections such as malaria, leishmaniasis and sleeping sickness.
A new efficient synthesis of GR24 and dimethyl A-ring analogues, germinating agents for seeds of the parasitic weeds Striga and Orobanche spp.
Malik, Heetika,Rutjes, Floris P.J.T.,Zwanenburg, Binne
experimental part, p. 7198 - 7203 (2010/10/02)
An efficient and high yielding preparation for the synthetic germination stimulant GR24 (5) and its A-ring dimethyl-substituted analogues 30-32 has been described. The first step involves a Stobbe condensation of benzaldehydes 9-11 with dimethyl succinate. Subsequent transposition of the ester and reduction of the double bond provides the building blocks 15-17 for an intramolecular Friedel-Crafts acylation. ABC-lactones 22-25 are prepared from γ-keto esters 18-21 by saponification, subsequent reduction with sodium borohydride followed by acid-catalyzed lactonization. Coupling of the lactones with the D-ring is accomplished by formylation and subsequent treatment with bromobutenolide 8 to give GR24 and its dimethyl analogues. Bioassays with Striga hermonthica seeds reveal that the dimethyl analogues are slightly less active than GR24 itself.
COMPOUNDS, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN TREATING METABOLIC DISORDERS
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Page/Page column 206, (2010/06/22)
The present invention is directed to novel compounds of formula (I) and their use in treating metabolic diseases.
Synthesis of versatile building blocks through asymmetric hydrogenation of functionalized itaconic acid mono-esters
Hekking, Koen F. W.,Lefort, Laurent,De Vries, Andre H. M.,Van Delft, Floris L.,Schoemaker, Hans E.,De Vries, Johannes G.,Rutjes, Floris P. J. T.
experimental part, p. 85 - 94 (2009/04/07)
The rhodium-catalyzed asymmetric hydrogenation of several β-substituted itaconic acid monoesters, using a library of monodentate phosphoramidite and phosphite ligands is described. Two β-alkylsubstituted substrates were readily hydrogenated by the rhodium complex Rh(COD) 2BF4 in combination with (S)-PipPhos as a ligand resulting in ees of 99 %. In contrast, the corresponding more hindered β-arylsubstituted substrates did not exhibit acceptable enantioselectivities under these conditions. However, the use of a 48-membered ligand library led to the identification of several suitable ligands for these substrates, resulting in ees of 89-99%. The resulting optically active succinic acid derivatives are potentially useful building blocks for more elaborate compounds, because of the ability to differentiate between the carboxylic acid and the ester groups on either side of the molecule.
Catalytic asymmetric alkynylation and arylation of aldehydes by an H 8-binaphthyl-based amino alcohol ligand
Ruan, Jiwu,Lu, Gui,Xu, Lijing,Li, Yue-Ming,Chan, Albert S. C.
experimental part, p. 76 - 84 (2009/04/11)
A novel chiral H8-1,1'-binaphthyl-based amino alcohol ligand (1Ra,2S,3R)-2 has been synthesized and applied in the direct nucleophilic addition of organozincs (alkynylzinc and arylzinc prepared in situ) to aldehydes, yielding the corresponding optically active propargylic alcohols and diarylmethanols in high yields and good to excellent enantioselectivities. For the asymmetric arylation reaction, one catalyst (1Ra,2S,3R)-2 can afford both enantiomers of many pharmaceutically interesting diarylmethanols by a proper combination of various arylzinc reagents and aldehydes.
A new target for highly stereoselective Katsuki-Sharpless epoxidation - One-pot synthesis of C2-symmetric 2,2′-bioxiranes
Bilenko, Vitaliy,Jiao, Haijun,Spannenberg, Anke,Fischer, Christine,Reinke, Helmut,Koesters, Jutta,Komarov, Igor,Boerner, Armin
, p. 758 - 767 (2008/02/07)
The double asymmetric Katsuki-Sharpless epoxidation of a conjugated diallyl alcohol affords excellent enantioselectivity (>97% ee), the product being isolated as the stable p-nitrobenzoate 5a or tosylate 5b. The optical purities of the chiral epoxides were determined by HPLC on chiral columns, while the molecular structures of compounds 5a and 7 and the absolute configuration of mono-epoxide 12 were confirmed by X-ray crystallography. Possible π-π stacking interaction has been evaluated by ab initio calculation. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
An Easy Procedure for the Preparation of 3-Methylidenetetrahydrofurans from Dimethyl Succinates
Corral, Jose M. Miguel,Gordaliza, Marina,Castro, M. Angeles,Salinero, Miguel A.,Dorado, Jose M.,Feliciano, Arturo San
, p. 154 - 164 (2007/10/03)
A new synthetic proceduree to obtain 3-methylidenetetrahydrofurans is described, in which the methylidene group is generated during the formation of the tetrahydrofuran ring. These are prepared by reduction of differently substituted dimethyl succinates obtained by Stobbe condensation.
Synthesis and Analgesic Effects of N--1-oxo-2(R)-benzylpropyl>-L-isoleucyl-L-leucine, a New Potent Inhibitor of Multiple Neurotensin/Neuromedin N Degrading Enzymes
Doulut, Sylvie,Dubuc, Isabelle,Rodriguez, M.,Vecchini, F.,Fulcrand, H.,et al.
, p. 1369 - 1379 (2007/10/02)
The synthesis of N--1-oxo-2(R)-benzylpropyl>-L-isoleucyl-L-leucine (JMV-390-1, 6a), a multipeptidase inhibitor based on the C-terminal sequence common to neurotensin (NT) and neuromedin N (NN), is described.This compound behaves as a full inhibitor of the major NT/NN degrading enzymes in vitro, e.g. endopeptidase 24.16, endopeptidase 24.15, endopeptidase 24.11, and leucine aminopeptidase (type IV-S), in the nanomolar range (IC50's from 30 to 60 nM).Compound 6a was found to increase endogenous recovery of NT and NN from slices of micehypothalamus depolarized with potassium.In various assays commonly used to select analgesics, e.g. hot-plate test, tail-flick test, acetic acid-induced writhing test, in mice, compound 6a proved to be potent when intracerebroventricularly (icv) injected.The analgesic effects observed were totally (hot-plate test) or largely (tail-flick test) reversed by the opioid antagonist naltrexone.Furthermore, icv injection of compound 6a (10 μg/mouse) was found to significantly potentiate the hypothermic effects of NT or NN.
Synthesis of Some Itaconates via Wittig Reaction
Awad, William I.,Kandile, Nadia G.,Wassef, Wasfy N.,Mohamed, Mansoura I.
, p. 405 - 410 (2007/10/02)
The Wittig reaction of aromatic aldehydes with 1,2-bis-(ethoxycarbonyl) ethylidene triphenyl phosphorane (1) furnished oily mixtures of the two diastereomeric products (E) and (Z) (2).Alkaline hydrolysis of the diesters followed by fractional crystallizat
