- High performance liquid chromatographic separation of clausenamide enantiomers with chiral-AGP stationary phase
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A method of high performance liquid chromatographic separation of clausenamide enantiomers with chiral-AGP (α1-acid glycoprotein) stationary phases has been established. The absolute configurations of (-)clausenamide and (+)clausenamide are 3S, 4R, 5R, 6S and 3R, 4S, 5S, 6R, respectively. The present method has been used to analyze the (-)clausenamide and (+)clausenamide and its analogues such as the major metabolite and synthetic derivatives of clausenamide.
- Wang, Yan,Yao, Qing Qiang,Wang, Mu Zou
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experimental part
p. 860 - 863
(2011/12/16)
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- Synthesis and activity in enhancing long-term potentiation (LTP) of clausenamide stereoisomers
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Clausenamide, isolated from aqueous extract of dry leaves of Clausena lansium, a Chinese folk medicine, was found to have potent activity in enhancing LTP and show nootropic activity in animal tests. In order to discovery more potent stereoisomers and to
- Feng, Zhiqiang,Li, Xingzhou,Zheng, Guojun,Huang, Liang
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scheme or table
p. 2112 - 2115
(2009/12/03)
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- Highly efficient and concise synthesis of both antipodes of SB204900, clausenamide, neoclausenamide, homoclausenamide and ζ-clausenamide. Implication of biosynthetic pathways of clausena alkaloids
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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.
- Yang, Luo,Wang, De-Xian,Zheng, Qi-Yu,Pan, Jie,Huang, Zhi-Tang,Wang, Mei-Xiang
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scheme or table
p. 2628 - 2634
(2009/10/31)
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- New procedures for the Julia-Colonna asymmetric epoxidation: Synthesis of (+)-clausenamide
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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.
- Cappi, Michael W.,Chen, Wei-Ping,Flood, Robert W.,Liao, Yong-Wei,Roberts, Stanley M.,Skidmore, John,Smith, John A.,Williamson, Natalie M.
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p. 1159 - 1160
(2007/10/03)
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- Diastereoselective and Enantioselective Total Synthesis of the Hepatoprotective Agent Clausenamide
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The diastereoselective total synthesis of the naturally ocurring hepatoprotective agent clausenamide (3-hydroxy-5-(α-hydroxybenzyl)-1-methyl-4-phenylpyrrolidin-2-one) is described, starting from ethyl cinnamate and diethyl acetamidomalonate.The enantioselective total synthesis of optically pure (+)-clausenamide is presented.The synthesis is based on a novel method for the preparation of optically pure (2S,3S)-3-phenylglutamic acid.
- Hartwig, Wolfgang,Born, Liborius
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p. 4352 - 4358
(2007/10/02)
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