17249-61-5

Usage

InChI:InChI=1/C12H12O4/c1-7(13)9-4-8-5-11(14-2)12(15-3)6-10(8)16-9/h4-6H,1-3H3

Upstream product

• 868856-45-5 (Z)-3-(3,4-dimethoxyphenoxy)-4-dimethylamino-3-buten-2-one 
• 26361-23-9 1-(3,4-dimethoxyphenoxy)propan-2-one 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 2033-89-8 3,4-dimethoxyphenol 
• 14382-91-3 2-hydroxy-4,5-dimethoxybenzaldehyde 
• 78-95-5 chloroacetone 
• 155955-78-5 3,4-dimethoxyphenylacetic acid N,O-dimethylhydroxyamide 
• 884-06-0 1-(3',4'-dimethoxyphenyl)-2-butanone 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 4460-86-0 asaraldehyde 
• 598-31-2 1-bromoacetone 

Relevant academic research and scientific papers

A novel, facile approach to frondosin B and 5-epi-liphagal via a new [4 + 3]-cycloaddition

A new [4 + 3]-cycloaddition between benzofuran allylic alcohols and dienes, promoted by camphorsulfonic acid, has been identified. A novel strategy which used this cycloaddition as a key step has been developed for the synthesis of 6,7,5-tricyclic skeleta

Synthesis of Benzo[ b]furans by Intramolecular C-O Bond Formation Using Iron and Copper Catalysis

One-pot processes for the synthesis of benzo[b]furans from 1-aryl- or 1-alkylketones using nonprecious transition metal catalysts have been developed. Regioselective iron(III)-catalyzed halogenation of the aryl ring, followed by iron- or copper-catalyzed O-arylation allowed the synthesis of various structural analogues, including the benzo[b]furan-derived natural products corsifuran C, moracin F, and caleprunin B.

BORONIC ACID BEARING LIPHAGANE COMPOUNDS AS INHIBITORS OF P13K- a AND/OR B

Compounds with unique liphagane meroterpenoid scaffold having boronic acid functionality in the skeleton are described (formula 1) together with pharmacological potential of these compounds as anticancer agents. A method of preparation and inhibiting the activity of phosphoinositide-3-kinase (PI3K-alpha and beta) has been presented. In particular, the invention describes a method of inhibiting PI3K isoforms, wherein the compounds are novel structures based on liphagane scaffold with unique boronic acid functionality. The methods and uses thereof are described herein this invention.

Efficient synthetic approach to substituted benzo[b]furans and benzo[b]thiophenes by iodine-promoted cyclization of enaminones

An efficient synthetic approach to the substituted benzo[b]furan and benzo[b]thiophene scaffolds by iodine-mediated cyclization of the corresponding enaminones is described. This protocol was applied to a large series of these latter precursors to afford the respective benzoheterocycles substituted at the C-2 position by a carbonyl group functionality. A study of the factors that control this process reveals that the reactivity depends on the presence of electron-donor groups in the aryl ring of the aryloxycarbonylic and arylthiocarbonylic moieties.

Total synthesis of (+/-)-frondosin B and (+/-)-5-epi-liphagal by using a concise (4+3) cycloaddition approach

A recently developed (4+3) cycloaddition between dienes and furfuryl alcohols, as precursors of oxyallyl-type cations, has been used as a key step in the racemic syntheses of two natural products: frondosin B and liphagal. This work demonstrates the synthetic potential of this cycloaddition reaction, and offers a short synthetic route to an interesting family of natural products. A full account of these synthetic studies is presented, further illustrating the mechanism, scope, and limitations of this straightforward synthetic method for seven-membered rings. Cycloheptanes: Furfuryl alcohols serve as effective three-carbon dienophiles for a wide range of dienes in stereoselective cycloaddition reactions. This efficient reaction has been used to prepare two cycloheptanoid natural products, offering a conceptually straightforward and short synthetic entry into a biologically interesting class of polycyclic meroterpenoids (see scheme; TFA = trifluoroacetic acid). Copyright

BORONIC ACID BEARING LIPHAGANE COMPOUNDS AS INHIBITORS OF PI3K-alpha AND/OR beta

Compounds with unique liphagane meroterpenoid scaffold having boronic acid functionality in the skeleton are described [formula 1] together with pharmacological potential of these compounds as anticancer agents. A method of preparation and inhibiting the activity of phosphoinositide-3-kinase (PI3K-alpha and beta) has been presented. In particular, the invention describes a method of inhibiting PI3K isoforms, wherein the compounds are novel structures based on liphagane scaffold with unique boronic acid functionality. The methods and uses thereof are described herein this invention. The claimed Markush formula is: [Formular 1], Y can be O, NH, NR, S; Representative compounds are: [Compounds A, B, C, D]

An efficient synthesis of benzofurans and their application in the preparation of natural products of the genus Calea

The intramolecular cyclization of the β-substituted olefins methyl 2-aryloxy-3-dimethylaminopropenoates 3a-3f catalyzed by Lewis acids leads to a short and novel synthesis of benzofurans 2a-2f. When the olefins 4-dimethylamino-3-aryloxy-3-buten-2-ones 4a-4f were used, the cyclization process was faster and provided the corresponding substituted 2-acetylbenzofurans 1a-1f. Among the latter, naturally occurring compounds calebertin (1a), caleprunin A (1b), and caleprunin B (1c) were prepared in good overall yields. These benzofurans were also obtained by direct treatment under MW irradiation of the precursors 1-aryloxypropan-2-ones 7a-7c with DMFDMA, followed by addition of the catalyst, resulting in a route that was one step shorter.