126452-80-0

Upstream product

• 75590-33-9 (-)-kaerophyllin 
• 126574-52-5 isokaerophyllin 
• 78473-72-0 3-(3,4-dimethoxybenzyl)-4-<3,4-methylenedioxy-α,α-bis(phenylthio)behzyl>butyrolactone 
• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 120-57-0 piperonal 
• 1432494-09-1 (E)-ethyl 4-(3',4'-dimethoxyphenyl)but-2-enoate 
• 5703-21-9 3,4-dimethoxyphenylacetaldehyde 
• 54844-36-9 3-(3,4-dimethoxyphenyl)propane-1,2-diol 
• 68996-81-6 3-benzo[1,3]dioxol-5-yl-propionyl chloride 
• 2815-95-4 3-(1,3 benzodioxol-5-yl)propionic acid 
• 93-15-2 1,2-dimethoxy-4-(2-propenyl)benzene 
• 7116-48-5 3-benzo[1,3]dioxol-5-yl-propionic acid ethyl ester 
• 24393-66-6 ethyl (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylate 
• 166884-72-6 1-(1-(allyloxy)-2-iodoethoxy)butane 

Relevant academic research and scientific papers

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.

Ni-Catalyzed Regioselective Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling and Application to the Concise Synthesis of Lignan Natural Products

We disclose a (terpy)NiBr2-catalyzed reaction protocol that regioselectively difunctionalizes unactivated olefins with tethered alkyl halides and arylzinc reagents. The reaction shows an excellent functional group tolerance (such as ketones, es

Trypanocidal structure-activity relationship for cis- and trans-methylpluviatolide

The trypanocidal activity of racemic mixtures of cis- and trans-methylpluviatolides was evaluated in vitro against trypomastigote forms of two strains of Trypanosoma cruzi, and in the enzymatic assay of T. cruzi gGAPDH. The cytotoxicity of the compounds w

Isolation, structure and synthesis of new diarylbutane lignans from Phyllanthus niruri: Synthesis of 5'-desmethoxy niranthin and an antitumour extractive

The structures of three new lignans (1-3) and a phenolic lignan (4) isolated from Phyllanthus niruri have been determined. The structures (1-3) were confirmed by their total synthesis and that of (4) was by its conversion to (3). The synthesis of (±) 5'-d

Isokaerophyllin, a butyrolactone from Bupleurum salicifolium

From the leaves of Bupleurum salicifolium two benzylidene-benzyl-γ-butyrolactone-type lignans were isolated. One was identified as kaerophyllin, the other as its cis-isomer, hitherto unreported. The latter was characterized as 2(3,4-dimethoxy)-benzylidene

Synthesis of Lignan Lactones by Conjugate Addition of Thioacetal Carbanions to Butenolide

The conjugate addition of carbanions derived from arylbis(phenylthio)methanes to butenolide followed by trapping of the enolate anion so generated by a benzyl halide affords adducts (8) containing the basic lignan skeleton.Desulphurisation of these adducts by Raney nickel affords a short efficient synthesis of trans-dibenzylbutyrolactones and this route has been used to prepare enterolactone (9c) and an antitumour lignan (9b), derived from Bursera schlechtendalii.Treatment of the adducts (8) with heavy-metal salts induces cyclisation leading to arylnaphthalene lactones, including retrojusticidin B (13).

A CONVERGENT MERCURY MEDIATED LIGNAN SYNTHESIS

Bis(thiophenyl) derivatives of dibenzylbutyrolactones undergo cyclisation elimination and dehydrogenation when treated with mercuric trifluoroacetate.The process is a short, efficient synthesis of certain arylnaphthalene lignans.