24192-64-1

Usage

InChI:InChI=1/C24H30O8/c1-25-17-7-13(8-18(26-2)23(17)29-5)21-15-11-32-22(16(15)12-31-21)14-9-19(27-3)24(30-6)20(10-14)28-4/h7-10,15-16,21-22H,11-12H2,1-6H3

Upstream product

• 77-78-1 dimethyl sulfate 
• 487-35-4 (+/-)-syringaresinol 
• 2373-80-0 3,4-methylenedioxy-trans-cinnamic acid 
• 20329-98-0 (E)-3,4,5-trimethoxy-cinnamic acid 
• 886989-84-0 (S)-1-[(E)-3-(3,4,5-trimethoxyphenyl)propenoyl]pyrrolidine-2-carboxylic acid 
• 886989-85-1 (1S,4S,5S,8S)-4,8-bis(3,4,5-trimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione 
• 886989-89-5 (1S,2R,3R,4S)-2,3-bis(hydroxymethyl)-1,4-bis(3,4,5-trimethoxyphenyl)butane-1,4-diol 
• 487-35-4 (+)-syringaresinol 
• 13060-14-5 (+)-yangambin 
• 487-35-4 (+)-(7S,7'R,8R,8'R)-4,4'-dihydroxy-3,3',5,5'-tetramethoxy-7,9':7',9-diepoxylignane 

Downstream Products

• 60619-98-9 (+)-syringaresinol dimethyl ether 
• 60619-98-9 (3aR)-1c,4t-bis-(2-bromo-3,4,5-trimethoxy-phenyl)-(3ar,6ac)-tetrahydro-furo[3,4-c]furan 

Relevant academic research and scientific papers

Electochemical asymmetric dimerization of cinnamic acid derivatives and application to the enantioselective syntheses of furofuran lignans

A new electrochemical method for the asymmetric oxidative dimerization of cinnamic acid derivatives has been developed. This method enabled the enantioselective syntheses of furofuran lignans, yangambin, sesamin and eudesmin.

Stereospecific synthesis of endo-endo-3,7-dioxabicyclo[3.3.0]octane lignans using 1,6-bis(dipropylboryl)-2,4-hexadiene

A general methodology for the stereoselective synthesis of compounds of the 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane series was developed. The strategy includes allylboration of aromatic aldehydes with 1,6-bis(dialkylboryl)-2,4- hexadiene, ozonolysis of the thus obtained 1,4-diaryl-2,3-divinyl-1,4-diols, and subsequent intramolecular cyclization. This methodology was used for obtaining the naturally occurring lignans of the furofuran series, viz., diaeudesmin, diayangambin, epiasarinin, epieudesmin, epiyangambin, and asarinin.

Stereoselective total synthesis of furofuran lignans through dianion aldol condensation

Highly stereoselective total synthesis of (+)-eudesmin, (+)-yangambin, (-)-eudesmin, and (-)-yangambin is described. This method is useful to generate the core skeleton of furofuran rings utilizing modification of Evans asymmetric aldol condensation.

Simple and efficient asymmetric synthesis of furofuran lignans yangambin and caruilignan A

A novel asymmetric dimerization of cinnamic acid derivative was achieved in high efficiency and high stereoselectivity. By using the reaction as a key step, two furofuran lignans, yangambin and caruilignan A were synthesized in optically pure form in only 5 and 6 steps, respectively. Georg Thieme Verlag Stuttgart.

Clay catalysed convenient isomerization of natural furofuran lignans under microwave irradiation

The naturally occuring furofuron lignans, (+)-sesamin, (+)-eudesmin, (+)-syringaresinol and (+)-yangambin underwent rapid isomerization to their corresponding C-7 epimers under microwave irradiation in the presence of montmorillonite KSF as catalyst.

Photoinduced molecular transformations. 157. A new stereo- and regioselective synthesis of 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans involving a β-scission of alkoxyl radicals as the key step. New total syntheses of (±)-sesamin, (±)-eudesmin, and (±)-yangambin

New total syntheses of naturally occurring 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans, (±)-sesamin and (±)-eudesmin, and the first total synthesis of (±)-yangambin were achieved according to a general method devised by Suginome and colleagues for replacing the carbonyl group of the cyclopentanone ring with an oxygen atom to give a corresponding tetrahydrofuran ring involving a regioselective β-scission of alkoxyl radicals; arylation of dimethyl, diallyl, or dibenzyl 3,7-dioxobicyclo[3.3.0]octane-2,6-dicarbonate (18 and 19a,b) with aryllead triacetate 9a-c, followed by dealkoxycarbonylation of the resulting arylated product 20a-f, gave 2,6-diaryl-3,7-dioxobicyclo[3.3.0]octane 21a-c. A regioselective Baeyer-Villiger oxidation of 21a-c with m-CPBA-NaHCO3 or -K2CO3 gave the corresponding δ-lactone 22a-c, which was reduced with DIBAL to give the corresponding lactol 23a-c. The irradiation of a solution of the hypoiodite of 23a-c, generated in situ with mercury(II) oxide-iodine, in benzene with Pyrex-filtered light resulted in a regioselective β-scission of the corresponding alkoxyl radical to give iodo formate 24a-c. Heating 24a-c in MeOH with NaBH4 gave (±)-sesamin (25a), (±)-eudesmin (25b), or (±)-yangambin (25c).