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.
Diastereodivergent Chiral Synthesis of the Furofuran Lignans (+)-Sesamin and (-)-Asarinin
Samizu, Kiyohiro,Ogasawara, Kunio
, p. 543 - 544 (1995)
Two diastereomeric lignans (+)-sesamin and (-)-asarinin have been prepared diastereodivergently via the common intermediate generated by the chirotopical Heck reaction.
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.
Synthesis of Lignans Based on a Borate-mediated One-pot Sequential Suzuki-Miyaura Coupling of Cyclic Boranes
Sato, Ko,Tanaka, Hiroshi
, p. 9422 - 9428 (2021)
Lignans are a group of polyphenolic phytochemicals that possess a large spectrum of chemical structures and biological activities. Here the syntheses of lignans – anwulignan, burseran, dehydroxycubebin, ruburisandrin B, and sesamin – are achieved based on a borate-mediated one-pot sequential Suzuki-Miyaura coupling of cis- and trans-fused bicyclic boranes, which were prepared by diastereoselective cyclic hydroboration of exo-cyclic diene with cyclopentyl- and thexylboranes, respectively. A one-pot sequential Suzuki-Miyaura coupling of each cyclic borate with various aryl bromides initiated by activation of the cyclic borane with the carbon nucleophile provided 2,3-dibenzylbutane derivatives with different aromatic substituents. Finally, the syntheses of naturally occurring lignans were accomplished in several steps from the products of Suzuki-Miyaura coupling.
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.
A Short Synthesis of (±)-Epiasarinin
Aldous, David J.,Dalencon, Anne J.,Steel, Patrick G.
, p. 1159 - 1161 (2002)
matrix presented Epiasarinin, an endo-endo furofuran, has been synthesized from piperonal via a five-step route with good stereocontrol. The sequence involves Darzens condensation, alkenyl epoxide-dihydrofuran rearrangement, and a Lewis acid mediated cyclization.
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.
A short and stereoselective total synthesis of (±)-sesamin by radical cyclisation of an epoxide using a transition-metal radical source
Rana,Guin,Roy
, p. 9337 - 9338 (2000)
A short, efficient and stereoselective synthesis of a furofuran lignan, (±)-sesamin, has been achieved in good overall yield through the radical cyclisation of an epoxide using a Ti(III) reagent as the radical initiator. (C) 2000 Elsevier Science Ltd.
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.
Reactions of lignan precursors, cinnamyl alcohols and cinnamic acids, with Weitz' aminium salt
Takeya,Ara,Tobinaga
, p. 1970 - 1976 (1995)
Reaction of a lignans precursor, cinnamyl alcohol (2a), with Weitz' aminium salt, tris(4-bromopheny)aminium hexachloroantimonate, in THF gave cinnamaldehyde (4), a coupling product (5), and a furofuran lignan, (±)- sesamin (6). Similar reactions using related precursors 2b, 3a, 3b gave 7, 8a, 9a, 10a, 11a, and 11b.
