40456-50-6

Usage

Uses

Used in Pharmaceutical Industry:
(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one is used as a bioactive compound for its ability to inhibit the cytochrome P450 (CYP) isoform CYP3A4, which plays a crucial role in drug metabolism. This property makes it a potential candidate for modulating drug interactions and improving the efficacy of other medications.
Used in Antiviral Applications:
In the field of antiviral research, (3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one is used to inhibit herpes simplex virus 1 (HSV-1) replication, as demonstrated by its activity in a plaque reduction assay.
Used in Cancer Therapy:
(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one is used as an apoptosis inducer and reactive oxygen species (ROS) producer in non-small cell lung cancer (NSCLC) cells, showing cytotoxic effects with IC50 values of 3.5 and 1.9 μM for A549 and CL1-5 cells, respectively. This makes it a potential therapeutic agent for the treatment of lung cancer.
Used in Cardiovascular Research:
In the cardiovascular field, (3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one is used to inhibit platelet aggregation induced by platelet-activating factor (PAF), collagen, or arachidonic acid. This property suggests its potential use in the development of anti-thrombotic agents to prevent blood clot formation and related disorders.
Overall, (3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one is a versatile compound with applications spanning from pharmaceuticals to antiviral and cardiovascular research, highlighting its potential impact on human health and disease treatment.

InChI:InChI=1/C22H24O7/c1-24-19-9-14(10-20(25-2)21(19)26-3)7-16-15(11-27-22(16)23)6-13-4-5-17-18(8-13)29-12-28-17/h4-5,8-10,15-16H,6-7,11-12H2,1-3H3/t15-,16+/m0/s1

Upstream product

• 80483-34-7 4-(1,3-benzodioxol-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one 
• 21852-50-6 3,4,5-trimethoxybenzyl bromide 
• 139448-51-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)allyl 2-bromo-3-(3,4,5-trimethoxyphenyl)propanoate 
• 118975-42-1 4-Benzenesulfonylamino-2-benzo[1,3]dioxol-5-ylmethyl-4-oxo-3-(3,4,5-trimethoxy-benzyl)-butyric acid 
• 66543-72-4 3-(3',4',5'-trimethoxyphenyl)propionyl chloride 
• 117824-56-3 wikstromol 
• 96548-65-1 3-(benzo[d][1,3]dioxol-5-ylmethyl)-4-methoxy-4-oxobutanoic acid 
• 58095-76-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-ol 
• 40918-96-5 methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate 
• 17187-77-8 (R)-(+)-3-piperonyl-4-butanolide 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 17301-91-6 cis-Dihydroanhydropodorhizol 
• 140138-39-2 (-)-(3S,4R,5R)-3-(3',4'5'-trimethoxybenzyl)-4-(3'',4''-methylenedioxybenzyl)-5-(1-menthyloxy)butyrolactone 
• 94-59-7 1-allyl-3,4-methylenedioxybenzene 

Downstream Products

• 477-51-0 rac-(7'β,8α,8'percentb)-3',4',5'-trimethoxy-4,5-methylenedioxy-2,7'-cyclolignan-9',9-olide 
• 119030-80-7 rac-(8α,8'β)-4'-hydroxy-3',5'-dimethoxy-3,4-methylenedioxylignan-9',9-olide 
• 72690-16-5 (3S,4S)-4-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(3,4,5-trimethoxybenzyl)dihydrofuran-2(3H)-one 
• 40456-50-6 yatein 
• 17187-81-4 (+)-isodeoxypodophyllotoxin 
• 477-51-0 deoxypodophyllotoxin 
• 17301-90-5 5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 
• 61038-90-2 (-)-isostegane 
• 73149-51-6 (-)-Dihydroclusin 
• 61038-90-2 trans-6-(hydroxymethyl)-10,11,12-trimethoxy-2,3-methylenedioxy-dibenzo[1a,4a:8a,12a]cyclooctadiene-7-carboxylic acid lactone 
• 60073-37-2 2'-bromo-dehydrodesoxypodophyllotoxin 
• 124252-78-4 2',6,6'-tribromoyatein 
• 93108-13-5 2′-bromodeoxypodophyllotoxin 
• 6258-43-1 4-benzo[1,3]dioxol-5-yl-5,6,7-trimethoxy-3H-naphtho[2,3-c]furan-1-one 

Relevant academic research and scientific papers

Asymmetric Chemoenzymatic Synthesis of (?)-Podophyllotoxin and Related Aryltetralin Lignans

(?)-Podophyllotoxin is one of the most potent microtubule depolymerizing agents and has served as an important lead compound in antineoplastic drug discovery. Reported here is a short chemoenzymatic total synthesis of (?)-podophyllotoxin and related aryltetralin lignans. Vital to this approach is the use of an enzymatic oxidative C?C coupling reaction to construct the tetracyclic core of the natural product in a diastereoselective fashion. This strategy allows gram-scale access to (?)-deoxypodophyllotoxin and is readily adaptable to the preparation of related aryltetralin lignans.

Chemoenzymatic Total Synthesis of Deoxy-, epi-, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones

Podophyllotoxin is probably the most prominent representative of lignan natural products. Deoxy-, epi-, and podophyllotoxin, which are all precursors to frequently used chemotherapeutic agents, were prepared by a stereodivergent biotransformation and a biocatalytic kinetic resolution of the corresponding dibenzylbutyrolactones with the same 2-oxoglutarate-dependent dioxygenase. The reaction can be conducted on 2 g scale, and the enzyme allows tailoring of the initial, “natural” structure and thus transforms various non-natural derivatives. Depending on the substitution pattern, the enzyme performs an oxidative C?C bond formation by C?H activation or hydroxylation at the benzylic position prone to ring closure.

TRIP-Catalyzed Asymmetric Synthesis of (+)-Yatein, (-)-α-Conidendrin, (+)-Isostegane, and (+)-Neoisostegane

The asymmetric allylation under the assistance of catalytic amounts of 3,3′-bis(2,4,6-triisopropylphenyl)-1,1′-binaphthyl-2,2′-diyl hydrogen phosphate (TRIP) allows the concise construction of the lignan scaffold from simple aldehydes and allylic bromides with full control of the two formed stereocenters. This young methodology has been employed to synthesize four naturally and pharmaceutically active lignans. Members of the dibenzylbutyrolactone, the tetraline, and the dibenzocyclooctadiene classes have been synthesized in 40-47% overall yield along four-step synthetic routes.

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

Catalytic Hydrogenolysis of Enantioenriched Donor–Acceptor Cyclopropanes Using H2 and Palladium on Charcoal

The hydrogenolysis of enantioenriched donor–acceptor (D–A) cyclopropanes using H2 (1 atm) and a catalytic amount of palladium on charcoal gave trans-α-alkoxycarbonyl-β-benzyl-γ-lactones or β-substituted γ-aryl-α,α-diesters with high enantiomeric excess. The reaction was also used as a key step in the asymmetric total synthesis of yatein with high ee and excellent dr. This demonstrates the utility of this new protocol for the asymmetric synthesis of trans-α,β-disubstituted γ-butyrolactones. D–A cyclopropanes containing electron-withdrawing groups at the β-position were not susceptible to hydrogenolysis under these conditions. The reductive ring-opening of a D–A cyclopropane using D2 instead of H2 generated the corresponding monodeuterated product.

Diastereoselective synthesis of β-piperonyl-γ-butyrolactones from Morita-Baylis-Hillman adducts. highly efficient synthesis of (±)-yatein, (±)-podorhizol and (±)-epi-podorhizol

Starting from a Morita-Baylis-Hillman adduct we describe a simple and very efficient method for the diastereoselective preparation of hydroxylated β-piperonyl-γ-butyrolactones. To exemplify the efficiency of this approach we also describe a highly efficie

Chiral Synthesis of Lignan Lactones, (-)-Hinokinin, (-)-Deoxypodorhizone, (-)-Isohibalactone and (-)-Savinin by Means of Enantioselective Deprotonation

Chiral synthesis of lignan lactones, (-)-hinokinin, (-)-deoxypodorhizone, (-)-isohibalactone and (-)-savinin, has been achieved by employing an enantioselective deprotonation of 3-(3,4-methylenedioxybenzyl)cyclobutanone with lithium (S,S')-α,α'-dimethylbenzylamide, as a key step.

Asymmetric Synthesis of Lignans of the Dibenzylbutanediol and Tetrahydrodibenzocyclooctene Series

Enolate anions obtained by conjugate addition to (-)-5-(1-menthyloxy)furan-2(5H)-one are quenched with benzyl bromides or iodides to yield homochiral dibenzylbutyrolactones.Desufurisation followed by lithium aluminium hydride reduction affords homochiral

Asymmetric Syntheses of Lignans of the Dibenzylbutyrolactone, Dibenzylbutanediol, Aryltetralin and Dibenzocyclooctadiene Series

General procedures are outlined for the asymmetric syntheses of ligands of the dibenzylbutyrolactone, dibenzylbutanediol, aryltetralin and dibenzocyclooctadiene series, from tandem addition products derived from 4-mentyloxybutenolide.