Averufin

Base Information

• Chemical Name: Averufin
• CAS No.: 14016-29-6
• Molecular Formula: C20H16 O7
• Molecular Weight: 368.343
• UNII: 7R1N64C5MZ
• DSSTox Substance ID: DTXSID10891789
• Wikidata: Q27139693
• ChEMBL ID: CHEMBL1706207
• Mol file: 14016-29-6.mol

Synonyms:3,4,5,6-Tetrahydro-7,9,11-trihydroxy-2-methyl-2,6-epoxy-2H-anthra(2,3-b)oxocin-8,13-dione;averufin

Chemical Property of Averufin

Chemical Property:

• Vapor Pressure: 3.94E-15mmHg at 25°C
• Boiling Point: 602.9°Cat760mmHg
• Flash Point: 220.8°C
• PSA: 113.29000
• Density: 1.585g/cm³
• LogP: 2.92900
• XLogP3: 3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 368.08960285
• Heavy Atom Count: 27
• Complexity: 665

Purity/Quality:

99% ^*data from raw suppliers

AVERUFIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC(O1)C3=C(O2)C=C4C(=C3O)C(=O)C5=C(C4=O)C=C(C=C5O)O
• Isomeric SMILES: C[C@]12CCC[C@H](O1)C3=C(O2)C=C4C(=C3O)C(=O)C5=C(C4=O)C=C(C=C5O)O
• General Description: Averufin is a key biosynthetic intermediate in the production of aflatoxin, a highly carcinogenic compound generated by certain Aspergillus fungi. Its structure features highly oxygenated aromatic rings, making it prone to rearrangement or degradation under acidic or basic conditions. The successful synthesis of averufin relies on protective strategies, such as methoxymethyl groups, to enable regiospecific aryl metalation and selective functionalization while maintaining stability. This approach facilitates the efficient production of averufin in its bioactive, unprotected form.

Technology Process of Averufin

There total 1 articles about Averufin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

methanol (67-56-1) + (1'S)-1'-O-β-D-galactofuranosyl-5'-oxoaverantin → methyl D-galactopyranoside (97-30-3,617-04-9,709-50-2,1824-94-8,2152-78-5,3149-68-6,3396-99-4,6819-48-3,18469-06-2,20550-04-3,22277-65-2,29411-57-2,35437-40-2,35437-43-5,36191-11-4,36191-12-5,39598-79-3,39598-80-6,39598-89-5,51023-63-3,51223-62-2,51224-38-5,51224-39-6,51224-40-9,51224-41-0,51819-81-9,51819-82-0,51819-83-1,56688-81-4,62279-53-2,64281-79-4,64281-80-7,64912-19-2,66101-73-3,78184-90-4,84368-39-8,84368-40-1,84368-41-2,92142-37-5,93302-26-2,103421-28-9,115794-08-6) + averufin (14016-29-6)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 42h;

DOI:10.1021/np500581m

Reference yield:

averufin (14016-29-6) → 1'-hydroxyversicolorone (111975-78-1)

Guidance literature:

Mechanism; mechanism of oxidation;

DOI:10.1016/S0040-4020(01)83431-1

Reference yield:

acetic anhydride (108-24-7) + averufin (14016-29-6) → avefurin triacetate (74810-25-6)

Guidance literature:

In pyridine; for 18h; Yield given; Ambient temperature;

upstream raw materials:

methanol

Downstream raw materials:

avefurin triacetate

1'-hydroxyversicolorone

Refernces

Methoxymethyl-Directed Aryl Metalation. A Total Synthesis of (+/-)-Averufin

10.1021/ja00413a018

The research described in the scholarly article presents a total synthesis of (f)-averufin, a key intermediate in the biosynthesis of aflatoxin, a potent carcinogen produced by certain strains of the fungus Aspergillus. The purpose of this study was to develop a method for synthesizing averufin in its fully unprotected, bioactive form, which is challenging due to the tendency of its highly oxygenated aromatic rings to rearrange or decompose under acidic or basic conditions. The researchers successfully achieved this by employing methoxymethyl protecting groups, which allowed for regiospecific aryl metalation and the selective introduction of electrophiles to simple oxygenated benzenoid precursors. The synthesis involved the regiospecific coupling of the phthalide anion of 3b and the benzyne derived from aryl bromide 4 to form the anthraquinone 5c, the immediate precursor to averufin. The use of methoxymethyl groups was crucial for protecting and deprotecting hydroxyl functions under mild conditions, enabling the synthesis of averufin with high yields and selectivity.

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