240420-40-0Relevant academic research and scientific papers
Synthesis of γ-oxo γ-aryl and γ-aryl α-amino acids from aromatic aldehydes and serine
Chacko, Shibin,Ramapanicker, Ramesh
, p. 7120 - 7128 (2013/02/21)
γ-Oxo α-amino acids and γ-aryl α-amino acids are compounds with very interesting biological properties and are active components of many drug molecules. Oxo amino acids are also used as synthetic precursors for a number of unnatural amino acids and amino alcohols. We report a very efficient synthesis of such compounds through the coupling of aromatic dithianes, prepared from aromatic aldehydes and an iodide derivative of serine. The dithiane groups in compounds thus obtained can be either hydrolyzed or reduced to generate 4-oxo-4-aryl or 4-aryl 2-amino butanol derivatives, respectively, which, on further transformations, can be converted into the title compounds. Starting with L-serine provides the corresponding D-amino acids with complete enantiopurity. The reported method is economically viable and complements the existing methods, which rely largely on cross-coupling reactions.
Palladium-catalyzed cross-coupling reactions in one-pot multicatalytic processes
Lebel, Helene,Ladjel, Chehla,Brethous, Lise
, p. 13321 - 13326 (2008/09/17)
Palladium-catalyzed cross-coupling reactions have been investigated in multicatalytic processes to synthesize disubstituted alkenes and alkanes from carbonyl derivatives. The use of copper-catalyzed methylenation reactions is the key starting reaction to produce terminal alkenes which are not isolated, but submitted to further structure elongation. Not only is the isolation of the alkene intermediate unnecessary, but also the copper catalyst is a beneficial cocatalyst in the palladium-catalyzed cross-coupling reactions. The desired products are thus typically obtained in higher yields using this one-pot approach. We have used these processes to synthesize hydroxylated (E)-stilbenoids, which are known chemopreventive and chemotherapeutic agents, odorant-substituted indanes, and non-natural amino acids, such as homophenylalanine.
Syntheses of sphingosine-1-phosphate analogues and their interaction with EDG/S1P receptors
Lim, Hyun-Suk,Park, Jeong-Ju,Ko, Kwangseok,Lee, Mee-Hyun,Chung, Sung-Kee
, p. 2499 - 2503 (2007/10/03)
Sphingosine-1-phosphate (S1P) is an important regulator of a wide variety of biological processes acting as an endogenous ligand to EDG/S1P receptors. In an effort to establish structure-activity relationship between EDG/S1P and ligands, we report herein
Heck reactions of amino acid building blocks: Application to the synthesis of pyrrololine analogues
Collier, Philip N.,Patel, Ian,Taylor, Richard J.K.
, p. 3401 - 3405 (2007/10/03)
Heck reactions of unsaturated amino acid building blocks are described which allow access to homo- and bis-homophenylalanine derivatives and to γ,δ-unsaturated amino acids. Preliminary synthetic studies utilising this chemistry for the preparation of pyrr
Enantiomerically pure α-amino acid synthesis via hydroboration - Suzuki cross-coupling
Collier, Philip N.,Campbell, Andrew D.,Patel, Ian,Raynham, Tony M.,Taylor, Richard J. K.
, p. 1802 - 1815 (2007/10/03)
The Garner aldehyde-derived methylene alkene 5 and the corresponding benzyloxycarbonyl compound 25 undergo hydroboration with 9-BBN-H followed by palladium-catalyzed Suzuki coupling reactions with aryl and vinyl halides. After one-pot hydrolysis -oxidation, a range of known and novel nonproteinogenic amino acids were isolated as their N-protected derivatives. These novel organoborane homoalanine anion equivalents are generated and transformed under mild conditions and with wide functional group tolerance: electron-rich and -poor aromatic iodides and bromides (and a vinyl bromide) all undergo efficient Suzuki coupling. The extension of this methodology to prepare meso-DAP, R,R-DAP, and R,R-DAS is also described.
The synthesis of novel amino acids via hydroboration-suzuki cross coupling
Campbell, Andrew D.,Raynham, Tony M.,Taylor, Richard J. K.
, p. 5263 - 5266 (2007/10/03)
The Gamer aldehyde-derived methylene alkene has been hydroborated using 9-BBN and the resulting organoborane employed in palladium-catalysed Suzuki coupling reactions to produce, after hydrolysis-oxidation, a range of novel amino acids as their N-BOC protected derivatives.
