114528-76-6

Basic information

• Product Name: (3S,4R,5R,6R)-epi-cis-clausenamide
• Synonyms: (3S,4R,5R,6R)-epi-cis-clausenamide
• CAS NO: 114528-76-6
• Molecular Weight: 297.354
• Mol File: 114528-76-6.mol

Chemical Properties

• CAS DataBase Reference: (3S,4R,5R,6R)-epi-cis-clausenamide(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R,5R,6R)-epi-cis-clausenamide(114528-76-6)
• EPA Substance Registry System: (3S,4R,5R,6R)-epi-cis-clausenamide(114528-76-6)

Safety Data

• Hazardous Substances Data: 114528-76-6(Hazardous Substances Data)

Upstream product

• 109838-83-7 (+/-)-(4R^*,5R^*,7S^*)-5-(α-hydroxybenzyl)-1-methyl-4-phenylpyrrolidin-2-one 
• 13992-75-1 5,5-Diethoxycarbonyl-4-phenylpyrrolidin-2-one 
• 109838-82-6 (+/-)-(4R^*,5R^*)-5-formyl-1-methyl-4-phenylpyrrolidin-2-one 
• 109838-81-5 (+/-)-(4R^*,5R^*)-5-(hydroxymethyl)-1-methyl-4-phenylpyrrolidin-2-one 
• 109838-84-8 (+/-)-(4R^*,5R^*)-5-benzoyl-1-methyl-4-phenylpyrrolidin-2-one 
• 109838-78-0 (2S,3R)-1-Methyl-5-oxo-3-phenyl-pyrrolidine-2,2-dicarboxylic acid ethyl ester 
• 109838-77-9 5,5-Diethoxycarbonyl-1-methyl-4-phenyl-pyrrolidin-2-one 
• 109838-79-1 (+/-)-(4R^*,5R^*)-5-(ethoxycarbonyl)-1-methyl-4-phenylpyrrolidin-2-one 
• 109838-83-7 (+/-)-(4R^*,5R^*,7R^*)-5-(α-hydroxybenzyl)-1-methyl-4-phenylpyrrolidin-2-one 
• 4192-77-2 ethyl cinnamate 
• 608122-68-5 (-)-3-deoxyepiclausenamide 
• 114376-13-5 (3S,4R,5R)-clausenamidone 
• 79898-18-3 (R)-α-methylbenzylammonium (2S,3R)-2,3-epoxy-3-phenylpropionate 
• 1566-68-3 (2RS,3SR)-2,3-epoxy-3-phenyl-propionic acid 

Downstream Products

• 109905-95-5 (±)-(3R,4S,5S,6R)-clausenamide 

Relevant articles and documents

Efficient synthesis of (-)-clausenamide

A new method for the synthesis of (-)-clausenamide was reported. (-)-clausenamide was obtained from the inexpensive material of trans-cinnamic acid within five steps with overall yields of 8.9% and ee 99.5%. Compared with the multi-step asymmetric synthes

Synthesis and activity in enhancing long-term potentiation (LTP) of clausenamide stereoisomers

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

Highly efficient and concise synthesis of both antipodes of SB204900, clausenamide, neoclausenamide, homoclausenamide and ζ-clausenamide. Implication of biosynthetic pathways of clausena alkaloids

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.

Diastereoselective and Enantioselective Total Synthesis of the Hepatoprotective Agent Clausenamide

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.