58005-36-0

Upstream product

• 2606-51-1 3,4-Methylenedioxybenzyl bromide 
• 603-35-0 triphenylphosphine 
• 495-76-1 piperonol 
• 120-57-0 piperonal 

Downstream Products

• 14522-89-5 4-(cis-2-benzodioxol-5-yl-vinyl)-3-(4-methoxy-phenyl)-sydnone 
• 14522-90-8 4-(trans-2-benzodioxol-5-yl-vinyl)-3-(4-methoxy-phenyl)-sydnone 
• 108907-01-3 (E)-5-(3-methoxystyryl)benzo[d][1,3]dioxole 
• 6091-43-6 all-trans-5-(3,4-Methylendioxyphenyl)-2,4-pentadiensaeureethylester 
• 891193-03-6 1-(3,4-methylenedioxyphenyl)-2-(2,4-di-O-tert-butyldimethylsiloxyphenyl)ethene oxide 
• 77669-23-9 (E)-2-(2-(benzo[d][1,3]dioxol-5-yl)vinyl)quinoline 
• 27951-92-4 2-(2-(benzo[d][1,3]dioxol-5-yl)vinyl)quinoline 
• 2030-55-9 (-)-zephyranthine 
• 1383713-49-2 5-(4-(4-methoxyphenyl)-3-methylbut-1-enyl)benzo[d][1,3]dioxole 
• 1383713-50-5 5-(4-(4-tert-butylphenyl)-3-methylbut-1-enyl)benzo[d][1,3]dioxole 
• 1383713-48-1 5-(4-(3-isopropylphenyl)pent-1-enyl)benzo[d][1,3]dioxole 
• 55038-30-7 (2E,4E,12E)-13-(benzo[d][1,3]dioxol-5-yl)-N-isobutyltrideca-2,4,12-trienamide 

Relevant academic research and scientific papers

Scalable total synthesis of horsfiequinone A

Starting from two commercially available substrates, methoxyhydroquinone and piperonyl alcohol, a scalable four-step total synthesis of horsfiequinone A was developed. The notable feature of the synthesis is the application of two continuous sequential transformations. Namely, the key aldehyde 9 and horsfiequinone A were prepared via scalable Wittig/hydrolysis and Wittig/catalytic hydrogenation/oxidation sequences, respectively. Importantly, the synthetic route required only three recrystallizations and one column chromatography purification step.

A concise and efficient synthesis of tetrahydroquinoline alkaloids using the phase transfer mediated Wittig olefination reaction

The present study describes the total synthesis of 1,2,3,4-tetrahydroquinoline alkaloids (±)-galipinine, (±)-cuspareine, (±)-galipeine and (±)-angustureine, in three steps and high yields (78%, 76%, 74%, and 66%, respectively) from common aldehyde and the ylide respectives. The key step of this approach is based on an unusual Wittig reaction by using the phase transfer medium (aq. NaOH/CH2Cl2 1:1 or t-BuOK/t-BuOH/CH2Cl2 1:1), affording olefinic intermediates in high yields.

Neuroprotective and Antineuroinflammatory Effects of Hydroxyl-Functionalized Stilbenes and 2-Arylbenzo[b]furans

The drugs currently used to treat Alzheimer’s disease (AD) are limited in the benefits they confer, and no medication has been clearly proven to cure or delay the progression of AD. Most candidate AD drugs are meant to reduce the production, aggregation,

GLYCOSIDASE INHIBITORS

Compounds of formula (I) wherein X1, X2, W, R1 to R5, L and m have the meaning according to the claims, are glucosidase inhibitors, and can be employed, inter alia, for the treatment of Alzheimer's disease.

Synthesis of combretastatin A4 analogues on steroidal framework and their anti-breast cancer activity

Combretastatin A4 analogues were synthesized on steroidal framework from gallic acid with a possibility of anti-breast cancer agents. Twenty two analogues were synthesized and evaluated for cytotoxicity against human breast cancer cell lines (MCF-7 & MDA-MB 231). The best analogue 22 showed potent antitubulin effect. Docking experiments also supported strong binding affinity of 22 to microtubule polymerase. In cell cycle analysis, 22 induced apoptosis in MCF-7 cells significantly. It was found to be non-toxic up to 300 mg/kg dose in Swiss albino mice in acute oral toxicity. This article is part of a Special Issue entitled "Synthesis and biological testing of steroid derivatives as inhibitors".

Asymmetric synthesis of 2-alkyl-substituted tetrahydroquinolines by an enantioselective aza-Michael reaction

An optically active tetrahydroquinoline intermediate (5) was prepared in 8 steps from monoprotected ethylene glycol, using a Pd-catalysed aza-Michael reaction to induce chirality. This can be transformed into three Galipea alkaloids (angustureine, galipeine and cuspareine). The proximity of a benzyloxy group is found to exert profound effects in several steps of the synthesis.

Synthesis of cicerfuran, an antifungal benzofuran, and some related analogues

Routes were investigated for the synthesis of cicerfuran, a hydroxylated benzofuran from wild chickpea implicated in resistance to Fusarium wilt, and some of its analogues. A novel method is described for the synthesis of oxygenated benzofurans by epoxidation and cyclisation of 2′-hydroxystilbenes. The stilbene intermediates required could be synthesised by palladium-catalysed coupling of styrenes with mono-oxygenated aryl halides but not with di-oxygenated aryl halides. Stilbenes corresponding to the latter were synthesised by Wittig reactions.

The first total synthesis of toddaquinoline, an alkaloid from Toddalia asiatica

The paper describes the first total synthesis of toddaquinoline, an alkaloid from the root bark of Formosan Toddalia asiatica. The key step is cobalt(I) mediated radial cyclisation to a pyridine. Cobalt appears to play a dual role in the reaction, firstly initialising homolysis of the carbon to halogen bond then acting as a Lewis acid to promote cyclisation to C-6. Other approaches examined are also outlined. These include a photocyclisation of an azastilbene; a cyclisation induced by halogen to metal exchange and a tin mediated radical cyclisation.

A practical and efficient synthetic route to dihydropipercide and pipercide

Dihydropipercide 1 and Pipercide 2 are examples of hydrophobic insecticidal isobutylamide derivatives isolated from Piper Nigrum L. which have received synthetic attention over the past decade. Novel structural features combining the N-isobutyldieneamide array, found in related natural products such as Pellitorine, with the 3,4-methylenedioxyphenyl moiety, found in insecticide synergists including Piperonyl Butoxide and Sesamex, render these as attractive targets for synthesis. Although a variety of synthetic routes to related natural products have appeared in the literature, practical methods for the preparation of the title compounds were lacking. Convenient and convergent 10-11-step protocols were developed which provided access to gram quantities of the targets. Methyl 6-oxohexanoate 4 was prepared from cyclohexanone enol acetate 3 via a tandem ozonolysis, methanolysis, hydrolysis process. Subsequent olefination and olefin isomerization steps followed by further elaboration provided the targets 1 and 2. Noteworthy features of this methodology include the convenient synthesis of oxoester intermediate 4 and the phenythio radical-induced olefin isomerization of intermediate 6 which afforded high yields of >99.5% E-olefin 13. These are both somewhat uncommon but potentially useful processes which may find further application in organic synthesis.

BIBENZYL DERIVATIVES FROM THE AUSTRALIAN LIVERWORT FRULLANIA FALCILOBA

Three new bibenzyl derivatives were isolated from the Australian liverwort Frullania falciloba and their structures were established to be 3,4-methylenedioxy-3'-methoxybibenzyl, 3-hydroxy-4,3'-dimethoxybibenzyl and 3--5,6-dimethoxyphthal