130273-47-1Relevant articles and documents
The preparation of optically active epineoclausenamide and enantiomeric separation of its racemate
Yan, Yixiao,Zhu, Senmei,Luo, Xuna,Rao, Yu,Su, Jinlong,He, Guantao,Lin, Hansen
, p. 643 - 651 (2021/08/24)
We synthesized the optically active epineoclausenamide by utilizing chiral reagents, such as R-α-methylbenzylamine and S-α-methylbenzylamine, for the resolution of the intermediate (trans-3-phenyl-oxiranecarboxylic acid 12), followed by amide exchange, cy
Highly efficient and concise synthesis of both antipodes of SB204900, clausenamide, neoclausenamide, homoclausenamide and ζ-clausenamide. Implication of biosynthetic pathways of clausena alkaloids
Yang, Luo,Wang, De-Xian,Zheng, Qi-Yu,Pan, Jie,Huang, Zhi-Tang,Wang, Mei-Xiang
experimental part, p. 2628 - 2634 (2009/10/31)
The synthesis of both antipodes of N-methyl-N-[(Z)-styryl]-3-phenyloxirane- 2-carboxamide (SB204900), clausenamide, neoclausenamide, homoclausenamide and ζ-clausenamide have been accomplished using (2S,3R)- and (2R,3S)-3-phenyloxirane-2-carboxamides as the starting materials, and SB204900 was found to be a common precursor to other N-heterocyclic clausena alkaloids. Mediated by Bronsted acids under different conditions, for example, SB204900 underwent efficient and diverse alkene-epoxide cyclization, enamide-epoxide cyclization and arene-epoxide cyclization reactions to produce the five-membered N-heterocyclic neoclausenamide, its 6-epimer, the six-membered N-heterocyclic homoclausenamide and the eight-membered N-heterocyclic ζ-clausenamide, respectively, in good to excellent yields. Regiospecific oxidation of neoclausenamide and its 6-epimer afforded neoclausenamidone. Enolization of neoclausenamidone in the presence of LiOH and the subsequent protonation under kinetic conditions at -78 °C led to the epimerization of neoclausenamidone into clausenamidone. Reduction of clausenamidone using NaBH4 furnished clausenamide in high yield. The Royal Society of Chemistry 2009.
New procedures for the Julia-Colonna asymmetric epoxidation: Synthesis of (+)-clausenamide
Cappi, Michael W.,Chen, Wei-Ping,Flood, Robert W.,Liao, Yong-Wei,Roberts, Stanley M.,Skidmore, John,Smith, John A.,Williamson, Natalie M.
, p. 1159 - 1160 (2007/10/03)
The oxidation of chalcone 1 to optically active epoxide 2 [a precursor of (+)-clausenamide (+)-3] may be effected using a 15-mer or 20-mer of L-leucine bound to a PEG based support; poly-L-leucines of this type may be used as immobilised catalysts in a fixed-bed reactor.
