16400-32-1Relevant articles and documents
Syntheses of Stereochemically Restricted Lactone-type Analogues of Jasmonic Acids
Toshima, Hiroaki,Aramaki, Hisateru,Ichihara, Akitami
, p. 1988 - 1992 (2000)
5-Oxa-7-epi-jasmonic acid and 5-oxa-jasmonic acid, which are stereochemically restricted lactone-type analogues of jasmonic acids, were synthesized via three-component coupling of 2(5H)-furanone, tert-butyl acetate and 1-bromo-2-pentyne. After acidic depr
Desymmetrisations of 1-alkylbicyclo[3.3.0]octane-2,8-diones by enzymatic retro-Claisen reaction yield optically enriched 2,3-substituted cyclopentanones
Hill, Cheryl L.,Verma, Chandra S.,Grogan, Gideon
, p. 916 - 924 (2007)
A series of 1-alkylbicyclo[3.3.0]octane-2,8-diones was transformed by enzymatic retro-Claisen reaction using recombinant 6-oxocamphor hydrolase (OCH) overexpressed in Escherichia coli, to yield optically active 2,3-substituted cyclopentanones with enantiomeric excesses of up to >95%. Whilst the parent substrate, bicyclo[3.3.0]octane-2,8-dione 12, was transformed only very slowly, derivatives 13, 14, 15, 16 and 30 with alkyl chains of varying length in the 1-position were converted rapidly to optically active products with typically 82% de and up to >95% enantiomeric excess. The results confirm the apparent requirement of OCH for non-enolisable diketone substrates, and offer a potential route to decorated cyclopentanone derivatives of multiple chiral centres. Computer modelling of 1-methylbicyclo-[3.3.0]octane-2,8-dione into the active site of OCH suggested that the bicyclic [3.3.0] series substrates were accommodated in the active site in similar orientation with the natural enzyme substrate, 6-oxo-camphor, and would thus yield the (2S,3S)-product series.
The handy use of brown's p2-ni catalyst for a skipped diyne deuteration: Application to the synthesis of a [D4]-labeled F4t- neuroprostane
Oger, Camille,Bultel-Ponce, Valerie,Guy, Alexandre,Balas, Laurence,Rossi, Jean-Claude,Durand, Thierry,Galano, Jean-Marie
, p. 13976 - 13980 (2010)
Brown's P2-Ni does the job: An efficient synthesis of tetradeuterated neuroprostane (see structure) has been accomplished by using an ene-diyne stereoselective deuteration strategy.
FATTY ACID DERIVATIVES AND THEIR USE
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Page/Page column 105, (2019/01/21)
This disclosure concerns fatty acid derivatives, pharmaceutical compositions comprising the fatty acid derivatives, and methods of using the fatty acid derivatives, for example, to treat inflammation, chronic itch, chronic pain, an autoimmune disorder, atherosclerosis, a skin disorder, arthritis, a neurodegenerative disorder, or a psychiatric disorder in a subject. In some embodiments, the fatty acid derivative is a compound, or a stereoisomer, tautomer, or pharmaceutically acceptable salt thereof, having a structure according to: (I) wherein X is from 1-16 carbons in length, Z is aliphatic from 1-16 carbons in length, or is not present, Y is selected from: (II) R1, R2, and R3 are independently hydrogen or lower alkyl, R4 is lower alkyl, hydroxyl, carboxyl, or amine, R5 is hydrogen, lower alkyl, or halide, R6 is hydroxyl or substituted thiol, and each R7 is independently hydrogen or fluoride or is not present and the adjacent carbons form alkyne.
Synthesis of Carbolines via Palladium/Carboxylic Acid Joint Catalysis
Cera, Gianpiero,Lanzi, Matteo,Balestri, Davide,Della Ca, Nicola,Maggi, Raimondo,Bigi, Franca,Malacria, Max,Maestri, Giovanni
supporting information, p. 3220 - 3224 (2018/06/11)
The combination of a Pd(0) complex with benzoic acid converts propargylic tryptamines to the corresponding tetrahydro-β-carbolines. The method uses unprotected indoles and affords the desired products with ample functional group tolerance. Detailed modeling studies reveal a close synergy between the organic and metal catalysts, which enables sequential alkyne isomerization, indole C-H activation, and eventual C-C reductive elimination to afford the target heterocycles.
Impaired energy processing disorders and mitochondrial deficiency
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Page/Page column 44, (2018/09/14)
Some aspects of the invention provide for a method of treating Impaired Energy Processing Disorders and Mitochondrial Deficiencies using polyunsaturated fatty acids which are modified in certain positions to attenuate oxidative damage by Reactive Oxygen Species (ROS) and/or suppress the rate of formation of reactive products and toxic compounds.
ALLEVIATING OXIDATIVE STRESS DISORDERS WITH PUFA DERIVATIVES
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Page/Page column 19-20, (2011/05/08)
Some aspects of the invention provide for essential fatty acids which are substituted in specific positions to slow down oxidative damage by Reactive Oxygen Species (ROS), and to suppress the rate of consequent formation of reactive products, for the purpose of preventing or reducing the damage associated with oxidative stress associated diseases such as neurological diseases and age-related macular degeneration (AMD).
Synthesis of carbazoles by gold(I)-catalyzed carbocyclization of 2-(enynyl)indoles
Praveen, Chandrasekaran,Perumal, Paramasivan Thirumalai
scheme or table, p. 521 - 524 (2011/04/17)
A new synthetic protocol for carbazoles through gold(I)-catalyzed intramolecular hydroarylation of (Z)-2-(enynyl)indoles was achieved in good yields. The requisite (Z)-2-(enynyl)indoles were synthesized stereoselectively by trimethylgallium-promoted, Z-selective Wittig olefination of N-alkylindole-2-carboxaldehydes with propargyl ylides. Substrates possessing both alkyl as well as aromatic groups are well tolerated under these reaction conditions. Georg Thieme Verlag Stuttgart.
Stereoselective total synthesis of (+)-mueggelone, a novel inhibitor of fish development
Yadav,Somaiah,Ravindar,Chandraiah
, p. 2848 - 2850 (2008/09/20)
An efficient stereoselective total synthesis of (+)-mueggelone, a novel inhibitor of fish development, is described. Highlights of the strategy include the utilization of Sharpless asymmetric epoxidation, Yamaguchi lactonization and an olefin cross-metathesis as the key steps.
An approach to 2,3-dihydropyrroles and β-iodopyrroles based on 5-endo-dig cyclisations
Knight, David W.,Redfern, Adele L.,Gilmore, Jeremy
, p. 622 - 628 (2007/10/03)
A representative series of homopropargylic sulfonamides 19 and 22b have been found to undergo smooth 5-endo-dig cyclisation upon exposure to excess iodine in acetonitrile containing potassium carbonate. The resulting 4-iodo-2,3-dihydropyrroles 23 readily react with two equivalents of DBU in DMF at 20°C to give the corresponding β-iodopyrroles 24 and 26 in excellent yields by the elimination of toluene-p-sulfinic acid. Use of less than two equivalents of base results in some loss of iodine. The iodo-2,3-dihydropyrroles 23 can be used in palladium-catalysed coupling reactions as shown by the efficient formation of the Sonogashira product 29 under mild conditions.
