1260604-96-3Relevant academic research and scientific papers
Divergent asymmetric synthesis of hexahydrobenzophenanthridine dopamine D1 agonists, A-86929, and dihydrexidine
Malhotra, Rajesh,Chakrabarti, Sagar,Ghosh, Amit,Ghosh, Rajib,Dey, Tushar K.,Dutta, Swarup,Dutta, Shantanu,Roy, Subho,Basu, Sourav,Hajra, Saumen
, p. 278 - 284 (2013/05/08)
A divergent and scalable asymmetric synthesis of the dopamine D1 agonists, A-86929, and dihydrexidine with high diastereo- and enantioselectivity was accomplished from Weinreb amide 8 derived from inexpensive and easily available l-serine. The synthesis of A-86929 involves only one chromatographic purification.
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.
