5211-23-4Relevant articles and documents
An efficient, stereocontrolled and versatile synthetic route to bicyclic partially saturated privileged scaffolds
Bond, Andrew D.,Hanby, Abigail R.,King, Thomas A.,Moss, Thomas A.,Sore, Hannah F.,Spring, David R.,Stewart, Hannah L.
supporting information, p. 6818 - 6821 (2020/07/04)
Herein, we describe the development of a simple, high yielding and stereocontrolled strategy for the synthesis of a series of triazolopiperazines and other biologically relevant fused scaffolds from optically active amino acids. This route was applied to the synthesis of 22 scaffolds containing new, previously inaccessible vectors and used to access a novel analogue of ganaplacide.
Efficient synthesis of methyl (S)-4-(1-methylpyrrolidin-2-YL)-3-oxobutanoate as the key intermediate for tropane alkaloid biosynthesis with optically acitve form
Katakam, Nanda Kumar,Seifert, Cole W.,D'Auria, John,Li, Guigen
, p. 604 - 613 (2019/08/01)
Methyl (S)-4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate has been synthesized for enzymatic studies on cyclization enzymes during cocaine biosynthesis in Erythroxylum coca plants. During the present new synthesis, L-proline was first protected with Cbz group and reduced to chiral amino alcohol, which were then followed by Swern oxidation, Wittig reaction and decarboxylative condensation. At the last step, N-methylamino acid precursor was treated with 1,1'-carbonyldiimidazole followed by reacting with methyl potassium malonate to give the 3-oxobutanoate in 54% overall yield. This new strategy has proven to avoid obvious racemization of the L-proline chiral center during the synthesis. In addition, six of the eight synthesis steps were performed via GAP chemistry/technology without the use of column chromatography for purification.
Iminium Catalysis inside a Self-Assembled Supramolecular Capsule: Modulation of Enantiomeric Excess
Br?uer, Thomas M.,Zhang, Qi,Tiefenbacher, Konrad
, p. 7698 - 7701 (2016/07/07)
The noncovalent combination of a supramolecular host with iminium organocatalysis is described. Due to cation–π interactions the reactive iminium species is held inside the host and reacts in this confined environment. The products formed differ up to 92 % ee from the control experiments without added host. A model rationalizing the observed difference is presented.
IDO INHIBITORS
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Paragraph 1621, (2016/10/27)
There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the invention.
A lanthanide(III) triflate mediated macrolactonization/solid-phase synthesis approach for depsipeptide synthesis
Goodreid, Jordan D.,Dos Santos Da Silveira, Eduardo,Batey, Robert A.
, p. 2182 - 2185 (2015/05/13)
The effect of dysprosium(III) triflate on macrolactonization reactions to form depsipeptides using MNBA (Shiina's reagent) is reported. Improved yields were obtained for the formation of 16-membered depsipeptides using lanthanide triflate additives. The use of a macrocyclization strategy permits the use of a semiautomated solid-phase synthesis approach for the rapid synthesis of analogues of the antibacterial A54556 acyldepsipeptides in only two physical operations, requiring only final product purification after cyclization.
Stereodivergent total synthesis of chlorofusin and its all seven chromophore diastereomers
Qiu, Hai-Bo,Qian, Wen-Jian,Yu, Shun-Ming,Yao, Zhu-Jun
, p. 370 - 380 (2015/02/19)
Chlorofusin (1), one of few natural antagonists against p53-MDM2 interactions, is a naturally biogenetic hybrid composed of a 27-membered nonacyclopeptide and a unique chromophore through the hydrocarbon linkage with ornithine. In this article, we describ
BIARYL INHIBITORS OF THE SODIUM CHANNEL
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Page/Page column 43, (2013/09/12)
The invention relates to compounds useful in treating conditions associated with voltage- gated ion channel function, particularly conditions associated with sodium channel activity. More specifically, the invention concerns biaryl derivatives (e.g., compounds according to any of Formulas (I)-(XII) or Compounds (l)-(372) of Table 1) that are that are useful in treatment of conditions such as epilepsy, cancer, pain, migraine, Parkinson's Disease, mood disorders, schizophrenia, psychosis, tinnitus, amyotropic lateral sclerosis, glaucoma, ischaemia, spasticity disorders, obsessive compulsive disorder, restless leg syndrome and Tourette syndrome.
Practical one-pot double functionalizations of proline
Huy, Peter,Schmalz, Hans-Guenther
experimental part, p. 954 - 960 (2011/05/07)
Solubilization of proline as the triethylammonium salt allows N-protection (as the Boc, Cbz or Moc derivative) and subsequent esterification or amidation of the carboxy terminus to be performed in an efficient one-pot fashion. Based on this concept, highly practical protocols were developed to prepare a series of proline derivatives (including Pro-Ser dipetides, Weinreb amides and N-protected proline esters), which are important intermediates, for instance, for the synthesis of proline-derived peptides, chiral reagents and catalysts for asymmetric synthesis. Georg Thieme Verlag Stuttgart - New York.
An efficient synthesis of sulfamides
Guo, Chuangxing,Dong, Liming,Kephart, Susan,Hou, Xinjun
scheme or table, p. 2909 - 2913 (2010/06/14)
Here we report an efficient synthesis of sulfamides. 3,5-Lutidine was found to be an optimal solvent and catalyst for the reaction. The method was developed during our efforts to synthesize a series of novel FKBP-12 inhibitors in which the known ketoamide linker was replaced with sulfamide.
PROCESS FOR PRODUCING CARBOXYLIC ACID FROM PRIMARY ALCOHOL
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Page/Page column 5-7, (2009/05/28)
To provide an industrially-useful and environmentally-friendly novel oxidation reaction. A process for producing a carboxylic acid from a primary alcohol, which comprises using an alkali metal chlorite as a co-oxidizing agent and using, as a catalyst, an oxoammonium salt of the formula (1):