114376-13-5

Upstream product

• 554420-04-1 (-)-clausenamidonyl (-)-menthoxyacetate 
• 114376-14-6 (3S,4R,5S)-neoclausenamidone 
• 121651-02-3 (2S,3R)-2-formyl-3-phenyloxirane 
• 104-55-2 3-phenyl-propenal 
• 115794-66-6 trans-methyl 3-phenylglycidate 
• 554420-01-8 (+)-(2S,3R)-N-methyl-N-(β-hydroxylphenethyl)-β-phenyl glycidic acid amide 
• 68579-60-2 2-(methylamino)-1-phenylethanol 
• 71403-94-6 2,3-epoxy-3-phenylpropanal 
• 4192-77-2 ethyl cinnamate 
• 121-39-1 (2S,3R)-ethyl 3-phenyloxirane-2-carboxylate 
• 14990-09-1 tert-butyl cinnamate 
• 1184725-14-1 (2S,3R)-3-phenyloxirane-2-carboxamide 
• 588-73-8 (Z)-β-bromostyrene 
• 1184725-15-2 C₁₇H₁₅NO₂ 

Downstream Products

• 595582-20-0 (-)-(3S,4S,5R,6S)-3-O-acetylclausenamide 
• 595582-21-1 (+)-(3S,4R)-3-O-acetyl-Δ^5,6clausenamide 
• 722525-97-5 (+)-(3S,4R)-Δ^5,6clausenamide 
• 722526-03-6 (-)-(3S,4S,5S,6R)-5-hydroxyclausenamide 
• 722526-09-2 (-)-(3S,4S,5R,6S)-5-hydroxyclausenamide 
• 595582-22-2 (-)-(3S,4S,5S,6R)-3-O-acetyl-5-hydroxyclausenamide 
• 595582-23-3 (-)-(3S,4S,5R,6S)-3-O-acetyl-5-hydroxyclausenamide 
• 595582-24-4 (-)-(3S,4S,5S)-3-O-acetyl-5-hydroxyclausenamidone 
• 595582-25-5 (-)-(3S,4S,5S,6S)-3-O-acetyl-5-hydroxyclausenamide 
• 595582-26-6 (-)-(3S,4S,5S,6S)-5-hydroxyclausenamide 
• 1579151-58-8 (-)-(3S,4S,5R)-3-O-acetylclausenamidone 
• 114528-76-6 (3S,4R,5R,6R)-epi-cis-clausenamide 

Relevant academic research and scientific papers

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

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.

An optical active wampi amide alkone and its derivatives

The invention discloses an optical active wampi amide alkone and its derivatives of the preparation method. The optical active wampi amide alkone preparation method comprises the following steps: S1. Racemic epoxy cinnamic acid synthesizing and; S2. (+) -

Optical-activity neoclausenamidone derivative and application thereof

The invention discloses an optical-activity neoclausenamidone derivative and application thereof. The structural formula of a compound is shown in the description (I), wherein R is C1-C4 paraffin, C2-C4 alkylene and C2-C4 alkyne or -COR1; R1 is selected f

Exploring tertiary enamides as versatile synthons in organic synthesis

Tertiary enamides have long been thought of as stable and marginally valuable enamine variants in synthesis. This notion has been challenged, however, in recent years. Enabling the regulation of the cross-conjugation system of the tertiary enamides has been successfully shown to enhance delocalization of the nitrogen lone-pair electrons into a carbon-carbon double, thereby reinvigorating the enaminic reactivity of the tertiary enamides. In this article, I summarize the recent advances in the exploration of the nucleophilic reactions of tertiary enamides and their applications in the synthesis of natural products and heterocyclic compounds of biological and pharmaceutical relevance, with a primary focus on our own work.

Method for Preparing Optically Pure (-)-Clausenamide Compound

Disclosed in the present invention is a method for preparing a (?)-clausenamide compound of formula (I), comprising: firstly, catalyzing the asymmetrical epoxidation of trans-cinnamate using a chiral ketone derived from fructose or a hydrate thereof as a catalyst, and then subjecting the product to transesterification, oxidation, cyclization and reduction successively to finally obtain the optically pure (?)-clausenamide compound of formula (I).

Highly efficient asymmetric synthesis of α,β-epoxy esters via one-pot organocatalytic epoxidation and oxidative esterification

Highly enantioselective synthesis of α,β-epoxy esters was achieved via one-pot organocatalytic epoxidation and consequent oxidative esterification. Excellent enantioselectivities (up to 99% ee) and good yields were obtained for a variety of α,β-epoxy esters. The method was readily scaled. Furthermore the product was applied towards the synthesis of (-)-clausenamide with excellent enantioselectivities (>99% ee).

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.