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
• Article Data: 8

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

• 1585241-66-2 (E)-methyl 6-methoxy-5-(2-nitrovinyl)picolinate 
• 1585241-79-7 C₁₀H₁₂N₂O₆ 
• 401792-87-8 methyl 5-formyl-6-methoxy-2-pyridinecarboxylate 
• 95652-81-6 6-chloro-2-methoxy-3-pyridinecarboxaldehyde 
• 17228-64-7 6-chloro-2-methoxypyridine 
• 1585241-73-1 (2S,3S,4S)-1-((benzyloxy)carbonyl)-3-(2-methoxy-2-oxoethyl)-4-(2-methoxy-6-(methoxycarbonyl)pyridin-3-yl)pyrrolidine-2-carboxylic acid 
• 1585241-72-0 C₂₄H₂₆N₂O₉ 
• 1585241-82-2 (2R,3S,4S)-1-benzyl 2-tert-butyl 3-(2-methoxy-2-oxoethyl)-4-(2-methoxy-6-(methoxycarbonyl)pyridin-3-yl)pyrrolidine-1,2-dicarboxylate 
• 2402-78-0 2,6-dichloropyridine 
• 1585241-71-9 methyl 5-((3S,4S,5R)-5-(tert-butoxycarbonyl)-4-(2-methoxy-2-oxoethyl)pyrrolidin-3-yl)-6-methoxypicolinate 
• 1585241-70-8 C₃₂H₃₆N₂O₇ 
• 1585241-69-5 (S)-5-benzhydryl 1-tert-butyl 3-((S)-1-(2-methoxy-6-(methoxycarbonyl)pyridin-3-yl)-2-nitroethyl)-2-oxopentanedioate 
• 1585241-68-4 5-benzhydryl 1-tert-butyl 2-oxopentanedioate 
• 1585241-81-1 C₄₀H₃₉O₄P 

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.

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.

Enantiospecific synthesis of acromelic acid A via a cobalt-mediated cyclisation reaction

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