94190-89-3

Usage

Uses

Used in Pharmaceutical Industry:
1-(2,3-Dihydroxy-4,6-diMethoxyphenyl)-1-propanone is used as a reactant for the preparation of Stigmatellin A (S686780), which may have potential applications in the development of new drugs and therapies.
Used in Chemical Research:
As a yellow solid with unique chemical properties, 1-(2,3-Dihydroxy-4,6-diMethoxyphenyl)-1-propanone can be utilized in chemical research to explore its properties, reactions, and potential applications in various chemical processes.

Preparation

Preparation by Fries rearrangement of 1,2-dihydroxy-3,5-dimethoxybenzene dipropionate with aluminium chloride in methylene chloride at r.t. for 3 h (94%).

Upstream product

• 94190-88-2 Propionic acid 2-hydroxy-4,6-dimethoxy-3-propionylphenyl ester 
• 21128-11-0 1,2-dihydroxy-3,5-dimethoxybenzene 
• 89880-48-8 1-(2,3,4,6-tetramethoxyphenyl)propan-1-one 
• 5333-45-9 1,2,3,5-tetramethoxybenzene 
• 293743-98-3 7-methoxy-2-phenyl-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 293744-00-0 7-methoxy-2-phenyl-benzo[1,3]dioxol-5-ol 
• 293743-99-4 7-methoxy-2-phenyl-benzo[1,3]dioxole-5-carbaldehyde 
• 293744-01-1 4,6-dimethoxy-2-phenyl-benzo[1,3]dioxole 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 500-99-2 3,5-dimethoxyphenol 
• 293744-02-2 propionic acid 2,4-dimethoxy-6-propionyloxy-phenyl ester 
• 293743-95-0 methyl 7-hydroxy-2-phenylbenzo[d][1,3]dioxole-5-carboxylate 
• 94190-87-1 1-(2-Hydroxy-4,6-dimethoxy-3-propionylphenyl)-1-propanone 
• 99-24-1 methyl galloate 

Downstream Products

• 276690-11-0 1-[2-hydroxy-4,6-dimethoxy-3-(methoxymethoxy)phenyl]propan-1-one 
• 293744-03-3 1-(3-benzyloxy-2-hydroxy-4,6-dimethoxy-phenyl)-propan-1-one 
• 276690-22-3 (2R,3S,4S,5S)-7-[5,7-dimethoxy-8-methoxymethoxy-3-methyl-4-oxo-4H-2-chromenyl]-2,4-dimethoxy-3,5-dimethylheptanol 
• 91682-96-1 stigmatellin A 
• 276690-20-1 (4S,5S,6S,7R)-8-Benzyloxy-5,7-dimethoxy-4,6-dimethyloctanoic acid 3,5-dimethoxy-2-methoxymethoxy-6-propionylphenyl ester 
• 276690-21-2 2-[(3S,4S,5S,6R)-7-Benzyloxy-4,6-dimethylheptyl]-5,7-dimethoxy-8-methoxymethoxy-3-methyl-4H-1-benzopyran-4-one 
• 293743-94-9 (2S,3S,4S)-6-(8-Benzyloxy-5,7-dimethoxy-3-methyl-4-oxo-4H-chromen-2-yl)-3-methoxy-2,4-dimethyl-hexanal 
• 293744-14-6 8-Benzyloxy-2-((3S,4S,5R)-6-hydroxy-4-methoxy-3,5-dimethyl-hexyl)-5,7-dimethoxy-3-methyl-chromen-4-one 
• 293743-92-7 (4S,5S,6R)-5-Methoxy-4,6-dimethyl-7-triisopropylsilanyloxy-heptanoic acid 2-benzyloxy-3,5-dimethoxy-6-propionyl-phenyl ester 
• 293744-13-5 8-Benzyloxy-5,7-dimethoxy-2-((3S,4S,5R)-4-methoxy-3,5-dimethyl-6-triisopropylsilanyloxy-hexyl)-3-methyl-chromen-4-one 

Relevant academic research and scientific papers

Formal total synthesis of stigmatellin A

An efficient and stereoselective approach for the formal total synthesis of Stigmatellin A has been described. The key steps involved in this synthesis are desymmetrization of the bicyclic olefin to introduce two methyl and two hydroxyl chiral centers, Fr

Diastereo- and enantioselective total synthesis of stigmatellin A

Stigmatellin A (1) isolated from the myxobacterium Stigmatella aurantiaca is a powerful inhibitor of electron transport in mitochondria and chloroplasts. The first highly diastereo- and enantioselective total synthesis of this important natural product is

Toward a total synthesis of stigmatellin; Obtention of an advanced fragment from gallic acid

Treatment by a base, then an acid, of the ester 3, which was prepared by starting from gallic acid 7a, afforded the chromone 6c, whose Swern oxidation, followed by condensation of the resulting aldehyde 6a with the trienyl lithium derivative 13b and methyl iodide, furnished products isomeric with, but not strictly identical to, an authentic sample of O-benzyl stigmatellin 1c. (C) 2000 Elsevier Science Ltd.

Antibiotics from Gliding Bacteria, XXIII. - Stigmatellin A and B - Two Novel Antibiotics from Stigmatella aurantiaca (Myxobacterales)

From the cells of the gliding bacterium Stigmatella aurantiaca strain Sg a15 two novel antibiotics named stigmatellin A and B were isolated as a mixture in addition to the known myxalamides.The structure elucidation of the crystalline main component A (7a