105661-97-0Relevant articles and documents
Clay catalysed convenient isomerization of natural furofuran lignans under microwave irradiation
Das,Madhusudhan,Venkataiah
, p. 4001 - 4006 (2000)
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.
An efficient and highly practical synthesis of tetrahydrofurofurane lignans
Chen, Bingzi,Ye, Xiulin,Chen, Qingqi
, p. 2831 - 2841 (1998)
A new route to tetrahydrofurofurane lignans 8 is present, which starts with substituted benzoate following a 7 step syntheses, and is distinctly shorter, more economic and efficient than any of the previous approaches to the target reported in the literature. The key step to establish the first furane ring 2 benefits the remarkable ease of the Diels-Alder reaction of 2,4-diaryloxazole 1 with 2-butyne-1,4-diol diacetate.
An efficient asymmetric synthesis of furofuran lignans: (+)-Sesamin and (-)-sesamin
Kim, Ju-Cheun,Kim, Kwang-Hyun,Jung, Jae-Chul,Park, Oee-Sook
, p. 3 - 6 (2006)
An efficient synthesis of (+)-sesamin 1a and (-)-sesamin 1b is described. The key reactions include highly stereoselective aldol condensation of piperonal 7 with the dianion of chiral oxazolidinone 8, followed by intramolecular ring cyclization of aldol product 11 in high yield.
Enantioselective total synthesis of furofuran lignans via Pd-catalyzed asymmetric allylic cycloadditon of vinylethylene carbonates with 2-nitroacrylates
Zhao, Can,Khan, Ijaz,Zhang, Yong Jian
, p. 12431 - 12434 (2020)
Herein, a practical and efficient approach to tetrahydrofurans with three-stereocenters has been developed through Pd-catalyzed asymmetric allylic cycloaddition of vinylethylene carbonates (VECs) with 2-nitroacrylates under mild conditions. By using this asymmetric catalytic reaction as a key step, several furofuran lignans with stereodivergency have been effectively synthesized through 5- or 6-step sequences from readily available starting materials.
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Beroza,Schechter
, p. 1242,1246 (1956)
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Stereospecific synthesis of endo-endo-3,7-dioxabicyclo[3.3.0]octane lignans using 1,6-bis(dipropylboryl)-2,4-hexadiene
Anfimov,Erdyakov,Gurskii,Bubnov
, p. 2336 - 2342 (2011)
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.
Chromatography-free “two-pots” asymmetric total synthesis of (+)-sesamin and (+)-aschantin
Hajra, Saumen,Garai, Sujay,Sen, Biswajit
, (2020/09/02)
A gram-scale chromatography-free asymmetric total synthesis of both homo- and heterobiaryl furofuran lignans containing at least one methylenedioxy phenyl unit such as (+)-sesamin and (+)-aschantin is accomplished in “two-pots” from easily accessible enantiopure lactone involving four steps in high overall yields. Steps- and pot economy are the key advantages of the protocol. Additionally, the bromo-functionality of the intermediates is useful for late stage functionalization.
Electochemical asymmetric dimerization of cinnamic acid derivatives and application to the enantioselective syntheses of furofuran lignans
Mori, Naoki,Furuta, Akiko,Watanabe, Hidenori
, p. 8393 - 8399 (2016/12/06)
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.
