28115-69-7

Upstream product

• 186581-53-3 diazomethane 
• 28115-67-5 Pluviatilol 
• 74-88-4 methyl iodide 
• 52200-05-2 4-methanesulfonyloxy-3-methoxybenzaldehyde 
• 651779-84-9 1-(4-methanesulfonyloxy-3-methoxyphenyl)prop-2-en-1-ol 
• 651779-83-8 (1S)-1-(4-methanesulfonyloxy-3-methoxyphenyl)prop-2-en-1-ol 
• 651779-86-1 (1S)-1-(4-methanesulfonyloxy-3-methoxyphenyl)allyl acetoacetate 
• 651779-87-2 (1R,4S,5S)-1-acetyl-4-(4-methanesulfonyloxy-3-methoxyphenyl)-3-oxabicyclo[3.1.0]hexan-2-one 
• 1105568-81-7 (1R,2S,5R,6S)-6-(3,4-dihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo-[3,3,0]octane 
• 86294-09-9 methyl 4,8-dimethoxy piperitol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 86279-03-0 (3R,3aR,6S,6aS)-3-Benzo[1,3]dioxol-5-yl-6-(3,4-dimethoxy-phenyl)-3a-methylsulfanyl-tetrahydro-furo[3,4-c]furan-1,4-diol 
• 86279-00-7 1-methylthio-8-piperonyl-4-veratryl-3,7-dioxabicyclo<3.3.0>octane-2,6-dione 
• 97141-82-7 (3R,3aR,6S,6aS)-6-Benzo[1,3]dioxol-5-yl-3-(3,4-dimethoxy-phenyl)-3a-methylsulfanyl-tetrahydro-furo[3,4-c]furan-1,4-diol 

Relevant academic research and scientific papers

HORSFIELDIN, A LIGNAN AND OTHER CONSTITUENTS FROM HORSFIELDIA IRYAGHEDHI

A new lignan, horsfieldin octane>, d-asarinin, (-)-dihydrocubebin, dodecanoylphloroglucinol, myristic acid, trimyristin and sitosterol have been isolated and charactreized from the hot methanol extract of Horsfieldia iryaghedhi seeds.The absolute configuration of the lignans and the chemotaxonomic significance of their occurence is discussed. - Key Word Index: Horsfieldia iryaghedhi; Myristicaceae; seeds; horsfieldin; d-asarinin; (-)-dihydrocubebin; dodecanoylphloroglucinol; myristic acid; trimyristin; sitosterol; structure elucidation; absolute configuratioon; chemotaxonomy.

A sterically encumbered photoredox catalyst enables the unified synthesis of the classical lignan family of natural products

Herein, we detail a unified synthetic approach to the classical lignan family of natural products that hinges on divergence from a common intermediate that was strategically identified from nature's biosynthetic blueprints. Efforts toward accessing the common intermediate through a convergent and modular approach resulted in the discovery of a sterically encumbered photoredox catalyst that can selectively generate carbonyl ylides from electron-rich epoxides. These can undergo concerted [3 + 2] dipolar cycloadditions to afford tetrahydrofurans, which were advanced (2-4 steps) to at least one representative natural product or natural product scaffold within all six subtypes in classical lignans. The application of those synthetic blueprints to the synthesis of heterolignans bearing unnatural functionality was demonstrated, which establishes the potential of this strategy to accelerate structure-activity-relationship studies of these natural product frameworks and their rich biological activity.

Stereocontrolled total syntheses of optically active furofuran lignans

Plant products (+)-sesamin, (+)-sesaminol, (+)-methylpiperitol, (+)-aschantin, and (+)-5'-hydroxymethylpiperitol were synthesized in a highly stereocontrolled manner through l-proline-catalyzed bifunctional-urea-accelerated cross-aldol reaction, followed by biomimetic construction of the furofuran lignan skeleton through a quinomethide intermediate.

A new synthetic entry to furofuranoid lignans, methyl piperitol and fargesin

An efficient and general process is described for the preparation ofthe unsymmetrically substituted diequatorial and axial-equatorial furofuran lignans, methyl piperitol and fargesin. The synthetic strategy is based on a stereoselective manner by nucleoph

A Versatile Stereoselective Synthesis of endo,exo-Furofuranones: Application to the Enantioselective Synthesis of Furofuran Lignans

A new stereoselective route to endo,exo-2,6-diarylfurofuranones has been developed using Mn(III)-mediated intramolecular cyclopropanation and C-H insertion reactions as key C-C bond-forming steps. Mn(III)-mediated oxidative cyclization of acetoacetate derivative 11 afforded 1-acetyl-4-aryl-3-oxabicyclo[3.1.0]hexan-2-one (12) with excellent diastereocontrol (d.r. 22:1). Subsequent Lewis acid-catalyzed opening of the activated cyclopropane ring present in 12 with benzylic alcohols then gave α-acetyl-γ-butyrolactones 16 and 18-20, which reacted efficiently with in situ-generated TfN3 to secure the key α-diazo-γ -butyrolactones 22-25. Highly stereoselective rhodium-catalyzed C-H insertion reactions of diazolactones 22-25 completed the synthesis of endo,exo-2,6-diarylfurofuranones 26-29 in overall yields ranging from 41 to 48% from 1-phenylallyl alcohol (±)-10. The approach developed for the furofuranones 26-29 was then applied to the asymmetric syntheses of four furofuran lignans, (+)-xanthoxylol (1), (+)-methylxanthoxylol (2), (+)-epipinoresinol (3), and (+)-epieudesmin (4), starting from enantiomerically enriched 1-arylallyl alcohol (S)-31.

Short and stereoselective total synthesis of furano lignans (±)-dihydrosesamin, (±)-lariciresinol dimethyl ether, (±)-acuminatin methyl ether, (±)-sanshodiol methyl ether, (±)-lariciresinol, (±)-acuminatin, and (±)-lariciresinol

Intramolecular radical cyclization of suitably substituted epoxy ethers 4a-g using bis(cyclopentadienyl)titanium(III) chloride as the radical source resulted in trisubstituted tetrahydrofurano lignans and 2,6-diaryl-3,7-dioxabicyclo [3.3.0] octane lignans depending on the reaction conditions. The titanium(III) species was prepared in situ from commercially available titanocene dichloride and activated zinc dust in THF. Upon radical cyclization followed by acidic workup, epoxy olefinic ethers 4a-g afforded furano lignans dihydrosesamin 1a, lariciresinol dimethyl ether lb, acuminatin methyl ether le, and sanshodiol methyl ether 1g directly and lariciresinol 1h, acuminatin li, and lariciresinol monomethyl ether 1j after removal of the benzyl protecting group by controlled hydrogenolysis of the corresponding cyclized products. The furofuran lignans sesamin 2a, eudesmin 2b, and piperitol methyl ether 2e were also prepared directly by using the same precursors 4a-f on radical cyclization followed by treatment with iodine and pinoresinol 2h, piperitol 2i, and pinoresinol monomethyl ether 2j after controlled hydrogenolysis of the benzyl protecting group of the corresponding cyclized products. Two naturally occurring acyclic lignans, secoisolariciresinol 5h and secoisolariciresinol dimethyl ether 5b, have also been prepared by exhaustive hydrogenolysis of 2h and 2b, respectively.

C-H insertion approach to the synthesis of endo,exo-furofuranones: Synthesis of (±)-asarinin, (±)-epimagnolin A, and (±)-fargesin

A series of novel 5-aryl-4-aryloxymethyl-3-diazotetrahydrofuran-2-ones (12, 24, and 35a/b) have been prepared and found to undergo regio- and stereoselective C-H insertion reactions to afford 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane-8-ones (18, 26, and 36a/b) with endo,exo stereochemistry. Subsequent reduction of the lactone ring and cyclization of the resulting diols 27 and 37a/b permitted the synthesis of three endo, exo-furofuran lignans: asarinin (2), fargesin (3), and epimagnolin A (4). En route to the key diazo compounds 24 and 35a/b, a modified procedure for the Ghosez keteniminium-olefin cyclization was developed, which was required to minimize the decomposition of acid-sensitive functional groups such as electron-rich benzylic ethers that were present in the target compounds 2-4.

Short and stereoselective total synthesis of (±)-dihydrosesamin and (±)-acuminatin methyl ether by radical cyclisation of epoxides using a transition-metal radical source

Short, efficient and stereoselective synthesis of a furano lignans, (±)- Dihydrosesamin and (±)-Acuminatin Methyl Ether has been achieved in good overall yield through the radical cyclisation of epoxides using a Ti(III) reagent as the radical initiator.

First Stereocontrolled Syntheses of Unsymmetrically Substituted Bislactone Lignans: Stereocontrolled Syntheses of Four Possible Isomers of Methyl 4,8-Dioxoxanthoxylol

An efficient method for stereocontrolled syntheses of the unsymmetrically substituted bislactone subgroup of the furofuran lignan has been developed based on a stereoselective aldol reaction of the acid anhydride 8 or 9 and an aromatic aldehyde employing

Stereocontrolled Syntheses of Diequatorial and Axial-Equatorial Furofuran Lignans

Methyl piperitol, a representative example of the diequatorial furofuran lignan, was synthesized in a good overall yield based on a highly stereocontrolled conjugate addition-aldol reaction.Fargesin, a representative example of the axial-equatorial furofu