130273-48-2

Upstream product

• 130202-78-7 (2R,3S)-N-methyl-N-(β-hydroxyphenylethyl)-3-phenyl-2,3-epoxypropionamide 
• 79898-19-4 (2R,3S)-3-phenyloxiranecarboxylic acid 
• 130273-47-1 (3R,4S,5R)-neoclausenamidone 
• 19190-80-8 cis-methyl 2,3-epoxy-3-phenylpropanoate 
• 554420-03-0 (+)-clausenamidonyl (-)-menthoxyacetate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 115794-67-7 methyl (2R,3S)-3-phenylglycidate 
• 104196-23-8 (2S,3S)-2,3-epoxy-3-phenyl-1-propanol 
• 173691-07-1 (2R,3S)-2,3-Dihydroxy-N-methyl-N-(2'-phenyl-1',3'-dithiolan-2'-ylmethyl)-3-phenylpropionamide 
• 173691-08-2 (2R,3S)-2,3-Epoxy-N-methyl-N-(2'-phenyl-1',3'-dithiolan-2'-ylmethyl)-3-phenylpropionamide 
• 173691-06-0 (4R,5S)--2,2-dimethyl-5-phenyl-1,3-dioxolane 
• 122743-18-4 methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate 
• 68579-60-2 2-(methylamino)-1-phenylethanol 
• 132490-26-7 (2R,3S)-phenyl 3-phenyloxirane-2-carboxylate 

Downstream Products

• 109905-95-5 (±)-(3R,4S,5S,6R)-clausenamide 
• 608128-73-0 (3R,4S,5S,6S)-epi-cis-clausenamide 
• 595582-27-7 (+)-(3R,4S,5S,6R)-3-O-acetylclausenamide 
• 722525-94-2 (-)-(3R,4S)-3-O-acetyl-Δ^5,6clausenamide 
• 722526-00-3 (-)-(3R,4S)-Δ^5,6clausenamide 
• 722526-12-7 (±)-(3R,4R,5S,6R)-5-hydroxyclausenamide 
• 722526-06-9 (-)-(3R,4R,5R,6S)-5-hydroxyclausenamide 
• 722526-17-2 (+)-(3R,4R,5R,6S)-3-O-acetyl-5-hydroxyclausenamide 
• 1579151-64-6 (+)-(3R,4R,5S,6R)-3-O-acetyl-5-hydroxyclausenamide 
• 722526-30-9 (+)-(3R,4R,5R)-3-O-acetyl-5-hydroxyclausenamidone 
• 722526-35-4 (+)-(3R,4R,5R,6R)-3-O-acetyl-5-hydroxyclausenamide 
• 595582-28-8 (±)-(3R,4R,5R,6R)-5-hydroxyclausenamide 
• 1579151-60-2 (+)-(3R,4S,5S)-3-O-acetylclausenamidone 

Relevant academic research and scientific papers

Enantiomeric resolution, thermodynamic parameters, and modeling of clausenamidone and neoclausenamidone on polysaccharide-based chiral stationary phases

The aim of the paper is to describe a new synthesis route to obtain synthetic optically active clausenamidone and neoclausenamidone and then use high-performance liquid chromatography (HPLC) to determine the optical purities of these isomers. In the process, we investigated the different chromatographic conditions so as to provide the best separation method. At the same time, a thermodynamic study and molecular simulations were also carried out to validate the experimental results; a brief probe into the separation mechanism was also performed. Two chiral stationary phases (CSPs) were compared with separate the enantiomers. Elution was conducted in the organic mode with n-hexane and iso-propanol (IPA) (80/20?v/v) as the mobile phases; the enantiomeric excess (ee) values of the synthetic R-clausenamidone and S-clausenamidone and R-neoclausenamidone and S- neoclausenamidone were higher than 99.9%, and the enantiomeric ratio (er) values of these isomers were 100:0. Enantioselectivity and resolution (α and Rs, respectively) levels with values ranging from 1.03 to 1.99 and from 1.54 to 17.51, respectively, were achieved. The limits of detection and quantitation were 3.6 to 12.0 and 12.0 to 40.0 ug/mL, respectively. In addition, the thermodynamics study showed that the result of the mechanism of chiral separation was enthalpically controlled at a temperature ranging from 288.15 to 308.15?K. Furthermore, docking modeling showed that the hydrogen bonds and π-π interactions were the major forces for chiral separation. The present chiral HPLC method will be used for the enantiomeric resolution of the clausenamidone derivatives.

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.

New procedures for the Julia-Colonna asymmetric epoxidation: Synthesis of (+)-clausenamide

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.

An asymmetric total synthesis of (+)-(3R,4S,5R,7S)-neoclausenamide

A new hepatoprotective lactam (+)-(3R,4S,5R,7S)-neoclausenamide 1 isolated from the leaves of Chinese folk medicine Clausena lansium (Lour.) Skeel, has been readily synthesized from methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate in 22.0% overall yield.

Asymmetric synthesis of (-)-dehydroclausenamide

Asymmetric synthesis of (-)-dehydroclausenamide 1 by scheme 2 was reported. Sharpless epoxidation was applied to cinnamyl alcohol for introduction of two desired chiral centers and the potential hydroxyl group. The key intermediate, γ-lactam (-)-5, was obtained by regio-selective intramolecular cyclization of (-)-6. Subsequent stereo-selective reduction was achieved by reducing C3-tetrahydropyranyl ether of (-)-5. The title natural product was then obtained by successive tosylation, hydrolysis and cyclization.