580-73-4

Upstream product

• 80483-34-7 4-(1,3-benzodioxol-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one 
• 2606-51-1 3,4-Methylenedioxybenzyl bromide 
• 24562-97-8 (E)-4-((benzo[d][1,3]dioxol-6-yl)methyl)-3-((benzo[d][1,3]dioxol-6-yl)methylene)dihy-drofuran-2(3H)-one 
• 24562-96-7 (2R*,3S*)-2,3-bis(3′,4′-methylenedioxybenzyl)butane-1,4-diol 
• 102001-95-6 trans-(+/-)-3,4-bis<(1,3-benzodioxol-5-yl)methyl>dihydro-2,5-furandione 
• 137809-97-3 2,3-di(3',4'-(methylenedioxy)benzyl)-2-buten-4-olide 
• 57420-27-6 2-piperonylsuccinic acid 
• 84736-29-8 dimethyl 2-[benzo(d)(1,3)dioxol-5-ylmethyl]succinate 
• 94839-07-3 3,4-(methylenedioxy)-benzeneboronic acid 
• 53762-69-9 5-(2-iodoethyl)-3,4-methylenedioxybenzene 
• 1383105-45-0 dimethyl 2-(2-(3,4-methylenedioxyphenyl)ethylidene)malonate 
• 1383105-47-2 dimethyl 2-(2-(3,4-methylenedioxyphenyl)-1-(pivaloyloxymethyl)ethyl)malonate 
• 1383105-49-4 methyl 4-(3,4-methylenedioxyphenylmethyl)-2-oxotetrahydrofuran-3-carboxylate 
• 1383105-53-0 dimethyl [2-(1,3-benzodioxol-5-yl)ethyl]malonate 

Downstream Products

• 81410-43-7 ariensin 

Relevant academic research and scientific papers

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.

Modular synthesis and biological investigation of 5-hydroxymethyl dibenzyl butyrolactones and related lignans

Dibenzyl butyrolactone lignans are well known for their excellent biological properties, particularly for their notable anti-proliferative activities. Herein we report a novel, efficient, convergent synthesis of dibenzyl butyrolactone lignans utilizing the acyl-Claisen rearrangement to stereoselectively prepare a key intermediate. The reported synthetic route enables the modification of these lignans to give rise to 5-hydroxymethyl derivatives of these lignans. The biological activities of these analogues were assessed, with derivatives showing an excellent cytotoxic profile which resulted in programmed cell death of Jurkat T-leukemia cells with less than 2% of the incubated cells entering a necrotic cell death pathway.

Radical one-pot α,β-dual and β-mono-oxymethylation of alkylidenemalonate

Dimethylzinc-mediated radical conjugate addition reaction of dimethyl alkylidenemalonates with iodomethyl pivalate gave a high yield of the α,β-dual oxymethylation product in one pot under air and the β-pivaloyloxymethylation product under argon.

Synthesis, anti-virus and anti-tumour activities of dibenzylbutyrolactone lignans and their analogues

An efficient synthesis of dibenzylbutyrolactone lignans and their analogues has been developed. Based on a Stobbe condensation of piperonal or veratraldehyde with diethylsuccinate and alkylation with 3,4- methylenedioxybenzyl bromide to give the skeleton

An efficient oxidative lactonization of 1,4-diols catalyzed by Cp*Ru(PN) complexes

An efficient oxidative lactonization of 1,4-diols in acetone is accomplished by the well-defined ruthenium catalyst, whose bifunctional nature underlies the high efficiency as well as unique chemo- and regioselectivity of the reaction which provides a rapid access to γ-butyrolactones including flavor lactones hinokinin, and muricatacin.

Double coupling reactions of 3,4-bis(stannyl)furanone: Facile preparation of diaryl- and dibenzylfuranones

The palladium-catalyzed cross-coupling reaction of 3,4-bis(tributylstannyl) furan-2(5H)-one using chelating ligand or polar solvent gives mixtures of single and double coupled products, even when one equivalent of halide coupling partner is used. After optimization, the double coupling reaction was shown to be general, with the use of two equivalents of aryl iodides giving 3,4-disubstituted furanones, The reaction using benzyl bromides proceeds at lower temperatures than the corresponding coupling using aryl iodides, giving dibenzylfuranones. The methodology has been exemplified in a synthesis of (±)-hinokinin. Georg Thieme Verlag Stuttgart.

Lipase-catalyzed esterification of a (±)-2,3-di(arylmethyl)-1,4- butanediol and its application to the synthesis of (S,S)-(+)-hinokinin

Racemic trans-2,3-di[(3,4-methylenedioxy)benzyl]-1,4-butanediol (dihydrocubebin) 6 was enantioselectively esterified using lipases as catalysts with vinyl acetate. Optically active (S,S)-1,4-butanediol 6 obtained was selectively oxygenated with a Fetizon reagent, affording (S,S)-(+)-hinokinin 9 in a high yield.

A novel asymmetric route to succinimides and derived compounds: Synthesis of the lignan lactone (+)-hinokinin

A novel approach to chiral succinimides and derived compounds has been developed that involves chiral lithium amide desymmetrisation of an N-ortho-tert-butylphenyl succinimide to generate a putative atropisomeric intermediate enolate, alkylation of which

A short synthesis of biologically active lignan analogues

β-Benzyl-γ-butyrolactones were synthesized in four transition metal catalysed reactions from butynediol, and alkylated to afford new, biologically active lignan analogues.

3-Phenylselanylfuran-2(5H)-one: A versatile building block in the synthesis of lignans. A new approach towards 3,4-dibenzyl γ-butyrolactones

Ready available 3-phenylselanylfuran-2(5H)-one undergoes tandem conjugate addition-alkylation by organocopper reagents to afford, with good yields and diastereoselectivities, 3,4-disubstituted-3-phenylselanyl-γ- butyrolactones, which can be transformed into naturally occurring compounds, such as lignans.