108210-83-9

Upstream product

• 1346555-96-1 (R,R,R,R)-N⁽¹⁾-methyl-2-(4-methoxyphenyl)-3-iodo-4-O-methoxymethyl-5-methylpyrrolidine 
• 67-56-1 methanol 
• 99878-83-8 (2R,3S,4S,5S)-bis<(methoxymethyl)oxy>-2-(p-methoxyphenyl)-1,5-dimethylpyrrolidine 
• 50-00-0 formaldehyd 
• 1615251-68-7 C₁₂H₁₇NO₃ 
• 628717-01-1 (2R,3R,4R,5R)-3,4-di-tert-butoxy-2-methyl-5-(4-methoxyphenyl)-N-hydroxypyrrolidine 
• 628716-88-1 (2R,3R,4R)-3,4-di-tert-butoxy-2-methyl-N-hydroxypyrrolidine 
• 934638-85-4 (R,E)-benzyl 5-(4-methoxyphenyl)-5-oxopent-3-en-2-ylcarbamate 
• 934638-89-8 (2R,3R,4R,5R)-1-(benzyloxycarbonyl)-2-(4-methoxyphenyl)-5-methylpyrrolidine-3,4-diyl diacetate 
• 521916-64-3 (2R,3R,4R,5R)-4-Methoxymethoxy-5-(4-methoxy-phenyl)-1,2-dimethyl-pyrrolidin-3-ol 
• 304850-95-1 (2R,3R,4R,5R)-N-(methoxycarbonyl)-3,4-dihydroxy-5-(methyl)-2-(p-methoxyphenyl)-pyrrolidine 
• 852310-65-7 tert-butyl 3,4-dihydroxy-2-(4-methoxyphenyl)-5-methyl-(2R,3R,4R,5R)-tetrahydro-1H-1-pyrrolecarboxylate 
• 108082-42-4 (2R,3S,4S,5S)-N-<(benzyloxy)carbonyl>-3,4-bis<(methoxymethyl)oxy>-2-(p-methoxyphenyl)-5-methylpyrrolidine 
• 108082-50-4 (3R,4S,5R)-3,4-bis<(methoxymethyl)oxy>-5-(p-methoxyphenyl)-5-(1,3-dioxo-2-azindan-2-yl)pentan-2-one 

Downstream Products

• 1615251-47-2 (2R,3R,4R,5S)-2-(4-methoxyphenyl)-1,5-dimethylpyrrolidine-3,4-diyl diacetate 

Relevant academic research and scientific papers

Design and total synthesis of (-)-codonopsinine, (-)-codonopsine and codonopsinine analogues by O-(2-oxopyrrolidin-5-yl)trichloroacetimidate as amidoalkylating agent with improved antimicrobial activity via solid lipid nanoparticle formulations

A general strategy towards total synthesis of (-)-codonopsinine, (-)-codonopsine and codonopsinine analogues has been developed from (D)-tartaric acid via the intermediate (3S,4R)-1-methyl-2-oxo-5-(2,2,2-trichloroacetamido)pyrrolidinediacetate (7). α-amidoalkylation studies of 7 with electron rich benzene derivative 8a-g as C-nucleophiles afforded (aryl derivatives) 9a-g. The target compounds 1, 2 and 13c-g were readily obtained from 10a-g via Grignard addition to the homochiral lactam which was produced by deoxygenation using Lewis-acid followed by deacetylation. The synthesized compounds were loaded onto solid lipid nanoparticle formulations (SLNs) prepared by hot emulsification-ultrasonication technique using Compritol as solid lipid and Pluronic f68 as surfactant. SLNs were fully evaluated and the permeation of synthesized compound from SLNs was assayed against non-formulated compounds through dialysis membranes using Franz cell. The data indicated good physical characteristics of the prepared SLNs, sustaining of release profiles and significant improvement of permeation ability when compared to the non-formulated compounds. The antibacterial and antifungal activities of 1, 2 and 13c-g were determined by disc diffusion and microbroth dilution method to determine the minimum inhibitory concentrations (MIC) against seven microorganisms (Staphyloccus aureus, Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Acinetobacter baumannii and Candida albicans). The most active compounds against the Gram positive S. aureus were 1, 13C, 13d, and 13g. Also, 13c, 13d, and 13e had antibacterial activity but not 13f against some Gram negative organisms (E. coli, and P. mirabilis). MIC concentrations against P. aeruginosa, and K. pneumoniae were ≥512 μg/ml, while that against A. baumannii was ≥128 μg/ml except for nanoformulae of 13e and 13f that were 16 and 64 μg/ml, respectively. No antifungal activity against Candida albicans was recorded for all compounds and their nanoformulae (MIC > 1024 μg/ml). SLNs were found to decrease the MIC values for some of the compounds with no effect on the antifungal activity. In conclusion, we demonstrated a novel, straight-forward and economical procedure for the total synthesis of (-)-codonopsinine 1, (-)-codonopsine 2 and codonopsinine analogues 13c-g from simple and commercially available starting materials; D-tartaric acid; with antimicrobial activities against Gram positive and Gram-negative organisms that were improved by SLNs formulations.

Heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis

A general and efficient method for heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis to access a wide range of structurally diverse oxygen as well as nitrogen heterocycles up to a gram scale is reported. The potential application of this new methodology is demonstrated by the total synthesis of (-)-codonopsinine and (+)-centrolobine. Herein it is proposed that selectfluor, unlike a fluorinating reagent, acts as an oxidative quencher and a hydrogen radical acceptor.

Total synthesis of (?)-codonopsinine via regioselective and diastereoselective amination using chlorosulfonyl isocyanate

The total synthesis of (?)-codonopsinine (1) from the readily available (S)-3-chloropropan-1,2-diol is described. The key steps for the preparation of (?)-codonopsinine (1) involve the regioselective and diastereoselective amination of anti-1,2-dibenzyl ether 11 using chlorosulfonyl isocyanate and intramolecular amidomercuration to form the pyrrolidine ring. Notably, the reaction between anti-1,2-dibenzyl ether and chlorosulfonyl isocyanate in toluene at 0 °C produced the corresponding anti-1,2-amino alcohol 12a as a major product with excellent diastereoselectivity (anti:syn = 29:1). This observation can be explained by the neighboring group participation leading to the retention of stereochemistry.

An easy route to synthetic analogues of radicamine B, codonopsine and codonopsinine from d-mannitol

A general strategy for the synthesis of analogues of radicamine B has been carried out from d-mannitol. This method has been further extended to the synthesis of analogues of codonopsine and codonopsinine using appropriate Grignard reagents. The hence obtained molecules have been tested against various commercially available glycosidases and found to act as moderate to good inhibitors. This journal is the Partner Organisations 2014.

Ring-closing iodoamination of homoallylic amines for the synthesis of polysubstituted pyrrolidines: Application to the asymmetric synthesis of (-)-codonopsinine

Ring-closing iodoamination of (E)-configured, N-α-methyl-p- methoxybenzyl protected homoallylic amines upon treatment with I2 and NaHCO3 in MeCN occurs with concomitant loss of the N-α-methyl-p-methoxybenzyl group to give 3-iodopyrrolidines in >99:1 dr. This transformation was used as one of the key steps in the total asymmetric synthesis of (-)-codonopsinine, which was achieved in seven steps (from commercially available tert-butyl crotonate) in 5% overall yield and >99:1 dr.

Asymmetric synthesis of (-)-codonopsinine

The asymmetric synthesis of (-)-codonopsinine was achieved in 7 steps (from commercially available tert-butyl crotonate) in 5% overall yield and >99:1 dr. The key step in this synthesis involved ring-closing iodoamination of a functionalised homoallylic a

Catalytic asymmetric direct henry reaction of ynals: Short syntheses of (2S,3R)-(+)-xestoaminol C and (-)-codonopsinines

Triple for all: Various optically active anti-β-nitro propargylic alcohols are synthesized by the catalytic stereoselective addition of nitroalkanes to ynals (the direct Henry reaction of ynals). The utilization of the rich chemistry of carbon-carbon triple bond allows rapid access to three natural products.

A short, efficient, and stereoselective total synthesis of a pyrrolidine alkaloid: (-)-Codonopsinine

An efficient total synthesis of antibiotic (-)-codonopsinine 1 with an overall yield of 44% was achieved from D-alanine as a chiral template. The key steps in our strategy are modified Sharpless asymmetric dihydroxylation reaction and the highly stereosel

Practical and highly stereoselective approaches to the total synthesis of (-)-codonopsinine

The enantiopure total synthesis of (-)-codonopsinine is described using two effective chiron approaches starting either from commercially available l-xylose or from readily available Garner aldehyde. The key steps included Julia trans-olefination, highly

Total synthesis of the alkaloid (-)-codonopsinine from L-xylose

The enantiopure total synthesis of (-)-codonopsinine is described from commercially available L-xylose in 20% overall yield. The key steps included Julia trans olefination and cascade epoxidation-cyclisation strategies.