2766-43-0Relevant articles and documents
Stereoselective synthesis of (-)-α-kainic acid and (+)-α-allokainic acid via trimethylstannyl-mediated radical carbocyclization and oxidative destannylation
Hanessian, Stephen,Ninkovic, Sacha
, p. 5418 - 5424 (1996)
(-)-α-Kainic acid (1) and its C4 epimer (+)-α-allokainic acid (2) have been prepared from L-serine. The requisite stereochemical array in (-)-α-kainic acid (1) was introduced using a trimethylstannyl radical carbocyclization of a diene, which gave the 2,3-trans/3,4-cis and 2,3-trans/3,4-trans componnds in a 2.8:1 ratio and in high yield. The destannylation of the trisubstituted pyrrolidine nucleus was achieved via an oxidative cleavage of the C-Sn bond with ceric ammonium nitrate. This provided a dimethyl acetal that was further transformed into the intended α-kainic acid. When the same radical carbocyclization was attempted on a triene, the 2,3-trans/3,4-trans and the 2,3-trans/3,4-cis adducts were obtained in a 2.5:1 ratio, respectively. This approach was used to synthesize (+)-α-allokainic acid.
Simple and efficient procedure for a multigram synthesis of both trans - And cis -1-Amino-2-(trifluoromethyl)cyclopropane-1-carboxylic Acid
Artamonov, Olexiy S.,Mykhailiuk, Pavel K.,Voievoda, Nataliia M.,Volochnyuk, Dmitry M.,Komarov, Igor V.
, p. 443 - 446 (2010)
A simple and efficient procedure for the multigram synthesis of both (±)-trans- and (±)-cis-1-amino-2-(trifluoromethyl)cyclopropane-1- carboxylic acid was developed. The key step of the synthesis is the addition of 1-diazo-2,2,2-trifluoroethane to methyl 2-[(tert-butoxycarbonyl)amino]acrylate, followed by thermal decomposition of the resulting pyrazoline. Gram quantities of trans- and cis-1-amino-2-(trifluoromethyl)cyclopropane-1-carboxylic acid were easily prepared from l-serine in one synthetic run. Georg Thieme Verlag Stuttgart - New York.
Synthesis and Biological Evaluation of CF3Se-Substituted α-Amino Acid Derivatives
Han, Zhou-Zhou,Dong, Tao,Ming, Xiao-Xia,Kuang, Fu,Zhang, Cheng-Pan
, p. 3177 - 3180 (2021/07/28)
Several CF3Se-substituted α-amino acid derivatives, such as (R)-2-amino-3-((trifluoromethyl)selanyl)propanoates (5 a/6 a), (S)-2-amino-4-((trifluoromethyl)selanyl)butanoates (5 b/6 b), (2R,3R)-2-amino-3-((trifluoromethyl)selanyl)butanoates (5 c/6 c), (R)-2-((S)-2-amino-3-phenylpropanamido)-3-((trifluoromethyl)selanyl)propanoates (11 a/12 a), and (R)-2-(2-aminoacetamido)-3-((trifluoromethyl)selanyl)propanoates (11 b/12 b), were readily synthesized from natural amino acids and [Me4N][SeCF3]. The primary in vitro cytotoxicity assays revealed that compounds 6 a, 11 a and 12 a were more effective cell growth inhibitors than the other tested CF3Se-substituted derivatives towards MCF-7, HCT116, and SK-OV-3 cells, with their IC50 values being less than 10 μM for MCF-7 and HCT116 cells. This study indicated the potentials of CF3Se moiety as a pharmaceutically relevant group in the design and synthesis of novel biologically active molecules.
Biocompatible Photoinduced Alkylation of Dehydroalanine for the Synthesis of Unnatural α-Amino Acids
Delgado, José A. C.,Correia, José T. M.,Pissinati, Emanuele F.,Paix?o, Márcio W.
supporting information, p. 5251 - 5255 (2021/07/20)
A site-selective alkylation of dehydroalanine to access protected unnatural amino acids is described. The protocol is characterized by the wide nature of alkyl radicals employed, mild conditions, and functional group compatibility. This protocol is further extended to access peptides, late-stage functionalization of pharmaceuticals, and enantioenriched amino acids.
