86630-09-3

Basic information

• Product Name: acromelic acid A
• Synonyms: acromelic acid A;(2S)-2α-Carboxy-4β-[(6-carboxy-2-oxo-1,2-dihydropyridin)-3-yl]pyrrolidine-3β-acetic acid;(2S)-3β-(Carboxymethyl)-4β-(2-oxo-6-carboxy-1,2-dihydropyridine-3-yl)pyrrolidine-2α-carboxylic acid;1,2-Dihydro-2-oxo-3-[(3S)-4α-(carboxymethyl)-5β-carboxypyrrolidin-3α-yl]pyridine-6-carboxylic acid;5-[(3S)-5β-Carboxy-4α-(carboxymethyl)pyrrolidin-3α-yl]-1,6-dihydro-6-oxopyridine-2-carboxylic acid;5-[(3S)-5β-Carboxy-4α-carboxymethylpyrrolidin-3α-yl]-1,6-dihydro-6-oxopyridine-2-carboxylic acid
• CAS NO: 86630-09-3
• Molecular Formula: C13H14N2O7
• Molecular Weight: 310.261
• Mol File: 86630-09-3.mol

Chemical Properties

• Boiling Point: 740.5°C at 760 mmHg
• Flash Point: 401.6°C
• Appearance: /
• Density: 1.577g/cm³
• Vapor Pressure: 5.44E-24mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: acromelic acid A(CAS DataBase Reference)
• NIST Chemistry Reference: acromelic acid A(86630-09-3)
• EPA Substance Registry System: acromelic acid A(86630-09-3)

Safety Data

• Hazardous Substances Data: 86630-09-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H14N2O7/c16-9(17)3-6-7(4-14-10(6)13(21)22)5-1-2-8(12(19)20)15-11(5)18/h1-2,6-7,10,14H,3-4H2,(H,15,18)(H,16,17)(H,19,20)(H,21,22)/t6-,7+,10-/m0/s1

Upstream product

• 103335-11-1 methyl (3S,4S,5S)-5-<1-(tert-butyloxycarbonyl)-4-<(methoxycarbonyl)methyl>-5-(methoxycarbonyl)-3-pyrrolidinyl>-1,6-dihydro-6-oxo-2-pyridinecarboxylate 
• 111563-56-5 tert-butyl (2S,3S,4S)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-(prop-1-en-2-yl)pyrrolidine-1-carboxylate 
• 111563-59-8 5-[(3S,4S,5S)-1-tert-Butoxycarbonyl-4-(2-hydroxy-ethyl)-5-hydroxymethyl-pyrrolidin-3-yl]-pyridine-2-carboxylic acid methyl ester 
• 103314-27-8 (3S,4S,5S)-1-(tert-butyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)oxy>methyl>-3-<2-<(tert-butyldimethylsilyl)oxy>ethyl>-4-(1-methylethenyl)pyrrolidine 
• 111563-57-6 (2S,3S,4R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(2-methyl-oxiranyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 103314-29-0 (3S,4S,5S)-2-<1-(tert-butyloxycarbonyl)-4-<2-<(tert-butyldimethylsilyl)oxy>ethyl>-5-<<(tert-butyldimethylsilyl)oxy>methyl>-3-pyrrolidinyl>acrylaldehyde 
• 109552-80-9 methyl (2S,3S,4S)-N-(tert-butoxycarbonyl)-3-methoxycarbonylmethyl-4-(2-methyl-5-pyridyl)-2-pyrrolidinecarboxylate 
• 109552-75-2 (R)-1-Benzyloxy-5-(6-methyl-pyridin-3-yl)-pent-4-yn-2-ol 
• 109552-79-6 (2R,3S,4S)-3-Methoxycarbonylmethyl-4-(6-methyl-pyridin-3-yl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 120976-35-4 (2S,3S,4S)-3-Carboxymethyl-4-(6-methoxycarbonyl-pyridin-3-yl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 
• 103314-31-4 (2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-((E)-4-oxo-1-phenylsulfanylmethyl-pent-2-enyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 103314-32-5 (2S,3S,4S)-4-((E)-1-Benzenesulfinylmethyl-4-oxo-pent-2-enyl)-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 401792-87-8 methyl 5-formyl-6-methoxy-2-pyridinecarboxylate 
• 1585241-79-7 C₁₀H₁₂N₂O₆ 

Relevant articles and documents

Practical total syntheses of acromelic acids A and B

Practical total syntheses of acromelic acids A (1) and B (2), which were scarce natural products isolated from toxic mushroom by Shirahama and Matsumoto, were accomplished in 13 (36% total yield) and 17 steps (6.9% total yield), respectively, from 2,6-dichloropyridine (8). Beginning with regioselective transformation of symmetric 8 by either ortho-lithiation or bromination, nitroalkenes 15 and 16 were provided. Stereoselective construction of the vicinal stereocenters at the C-3, 4 positions of 1 and 2 was performed by a Ni-catalyzed asymmetric conjugate addition of α-ketoesters to the nitroalkenes. Construction of the pyrrolidine ring was accomplished in a single operation via a sequence consisting of reduction of the nitro group, intramolecular condensation with the ketone, and reduction of the resulting ketimine.

Practical total syntheses of acromelic acids A and B

Practical total syntheses of acromelic acids A (1) and B (2), which have potent neuro-excitatory activity, were accomplished in 13 (36% total yield) and 17 steps (6.9% total yield), respectively, from 2,6-dichloropyridine (8). Regioselective transformation of symmetric 8 provided nitroalkenes 15 and 16. The pyrrolidine ring was efficiently constructed by Ni-catalyzed asymmetric conjugate addition followed by intramolecular reductive amination.

Concise syntheses of acromelic acid A and allo-acromelic acid A

Acromelic acid A 1 and allo-acromelic acid A 12 were synthesised in a biomimetic fashion. An oxidative cleavage-recyclisation strategy was used to construct the requisite C-4 pyridone from an intermediate catechol.

A biomimetic approach to the pyridone rings of the acromelic acids: A concise synthesis of acromelic acid a and an approach to acromelic acid B.

The syntheses of acromelic acid A 1, allo-acromelic acid A 19 and an approach towards acromelic acid B 2 are described. Palladium (0) catalysed cross-coupling reactions were used to generate C-4 catechol precursors and formation of the pyridone rings was investigated using a biomimetic oxidative cleavage - recyclisation strategy.

SYNTHESIS OF ACROMELIC ACID A, A TOXIC PRINCIPLE OF CLITOCYBE ACROMELALGA.

Acromelic acid A, a toxic principle of Clitocybe acromelalga, was synthesized from L-α-kainic acid.The synthesis established the previously inferred structure, and determined the absolute configuration as shown by 1.