13062-78-7Relevant articles and documents
Total synthesis of a lignanamide from Aptenia cordifolia
Xia, Yamu,Li, Chenchen,Zhang, Huaizheng,Lin, Jiao,Chai, Chen
, p. 535 - 538 (2015)
(E,E)-N,N-Dityramin-4,4'-dihydroxy-3,5'-dimethoxy-ss,3'-bicinnamamide, a lignanamide isolated from Aptenia cordifolia, was synthesised from vanillin and tyramine. The key 8-5'-neolignan intermediate diacid was formed efficiently using oxidative coupling of the ferulic acid derivatives and the ring-opening reaction of a dihydrobenzofuran.
Biomimetic synthesis of galantamine: Via laccase/TEMPO mediated oxidative coupling
Baratto, Maria Camilla,Bizzarri, Bruno Mattia,Botta, Lorenzo,Pogni, Rebecca,Saladino, Raffaele,Zippilli, Claudio
, p. 10897 - 10903 (2020/03/27)
Laccase-mediated intramolecular oxidative radical coupling of N-formyl-2-bromo-O-methylnorbelladine afforded a novel and isolable spirocyclohexadienonic intermediate of galantamine. High yield and conversion of substrate were obtained in the presence of the redox mediator 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO). This laccase procedure, with an overall yield of 34%, represents a scalable and environmentally friendly alternative to previously reported syntheses of galantamine based on the use of potassium ferricyanide as an unspecific radical coupling reagent.
Organocatalytic Decarboxylation of Amino Acids as a Route to Bio-based Amines and Amides
Claes, Laurens,Janssen, Michiel,De Vos, Dirk E.
, p. 4297 - 4306 (2019/08/26)
Amino acids obtained by fermentation or recovered from protein waste hydrolysates represent an excellent renewable resource for the production of bio-based chemicals. In an attempt to recycle both carbon and nitrogen, we report here on a chemocatalytic, metal-free approach for decarboxylation of amino acids, thereby providing a direct access to primary amines. In the presence of a carbonyl compound the amino acid is temporarily trapped into a Schiff base, from which the elimination of CO2 may proceed more easily. After evaluating different types of aldehydes and ketones on their activity at low catalyst loadings (≤5 mol%), isophorone was identified as powerful organocatalyst under mild conditions. After optimisation many amino acids with a neutral side chain were converted in 28–99 % yield in 2-propanol at 150 °C. When the reaction is performed in DMF, the amine is susceptible to N-formylation. This consecutive reaction is catalysed by the acidity of the amino acid reactant itself. In this way, many amino acids were efficiently transformed to the corresponding formamides in a one-pot catalytic system.
