50544-08-6

Upstream product

• 50394-05-3 (7S,8S,7′R,8′R)-3,3′,4,4′,5,5′-hexamethoxy-7,7′,8,8′-lignan 
• 186581-53-3 diazomethane 
• 20675-95-0 (E)-2,6,-dimethoxy-4-(prop-1-en-1-yl)phenol 
• 66280-26-0 pre-gomisin 
• 93395-16-5 (3S*,4R*)-3-(3,4,5-trimethoxybenzyl)-4-(3,4,5-trimethoxybenzyl)-4,5-dihydro-2(3H)-furanone 
• 487-11-6 elemicin 
• 121637-68-1 1-(3,4,5-trimethoxyphenyl)-2-bromopropane 
• 1369589-13-8 (Z)-5-(2-iodoprop-1-enyl)-1,2,3-trimethoxybenzene 
• 1369589-16-1 5,5'-((1Z,3Z)-2,3-dimethylbuta-1,3-diene-1,4-diyl)bis(1,2,3-trimethoxybenzene) 
• 5658-50-4 1-(3,4,5-trimethoxyphenyl)propan-1-one 
• 29652-81-1 1-(3,4,5-trimethoxyphenyl)-1-propanol 
• 138613-39-5 (2RS,3SR)-2,3-dimethyl-1,4-bis(3,4,5-trimethoxyphenyl)butan-1-one 
• 104385-15-1 1,4-bis(3,4,5-trimethoxyphenyl)-2,3-dimethyl-2,3-butanediol 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 

Downstream Products

• 61281-38-7 (+/-)-deoxyschizandrin 
• 1379671-31-4 5,5'-(2,3-dimethylbutane-1,4-diyl)bis(4-bromo-1,2,3-trimethoxybenzene) 
• 1379671-32-5 5,5'-(2,3-dimethylbutane-1,4-diyl)bis(4-iodo-1,2,3-trimethoxybenzene) 
• 14335-63-8 (1α,2β,3α)-6,7,8-trimethoxy-2,3-dimethyl-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene 
• 61281-38-7 (+/-)-1,2,3,10,11,12-hexamethoxy-r-6,t-7-dimethyl-5,6,7,8-tetrahydrodibenzocyclooctene 
• 14335-63-8 (1α,2β,3β)-6,7,8-trimethoxy-2,3-dimethyl-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene 
• 156769-17-4 schisandrin A 
• 115495-71-1 (+/-)Deoxyschizandrin 

Relevant academic research and scientific papers

A concise total synthesis of deoxyschizandrin and exploration of its antiproliferative effects and those of structurally related derivatives

The natural product deoxyschizandrin has been shown to have a wide range of biological activities. In recent years the therapeutic potential of this compound against cancers has attracted significant interest. Herein we describe a concise de novo total synthesis of deoxyschizandrin based around a double organocuprate oxidation strategy. In addition, we present the results of biological studies exploring the ability of deoxyschizandrin and synthetic precursors lacking the medium ring biaryl unit to inhibit the proliferation of a human cancer cell line. These studies led to the identification of a structurally novel agent with in vitro anticancer activity. Copyright

Structure-activity relationships of lignans from Schisandra chinensis as platelet activating factor antagonists

We studied the structure-activity relationships of lignans from Schisandra chinensis and their derivatives as platelet activating factor (PAF) antagonists. Strong activity was shown in lignans without an ester group at C-6, a hydroxyl group at C-7 or a methylene dioxy moiety and with an R-biphenyl configuration. 6(7)-Dehydroschisandrol A, a derivative of schisandrol A, showed the highest activity (IC50, 2.1 x 10-6 M) in this study.

Intramolecular Oxidative Coupling of Aromatic Compounds. VI. An Efficient Synthesis of Some Dibenzocyclooctene Lignans

The 1,4-diaryl-2,3-dimethylbutanes (4) and (5) were readily prepared by reductive coupling of an arylacetone precursor followed by hydrogenation.Intramolecular oxidative coupling (dichlorodicyanobenzoquinone/trifluoroacetic acid) gave dibenzocyclooctene derivatives in good yield. (+/-)-Deoxyschizandrin and the corresponding trans isomer, existing in two distinct conformations, were prepared.

Ruthenium dioxide in fluoro acid medium V. Application to the non phenolic oxidative coupling of diarylbutanes. Conformational studies of cis and trans deoxyschizandrins

Ruthenium (IV) dioxide dihydrate in fluoro acidic medium was found to be a very efficient agent for the non phenolic oxidative coupling of diarylbutanes. We observed along with the expected aryl-aryl coupling, an unusual aryl-benzyl coupling, leading to a known class of lignans, the aryltetralins. Conformational studies of resultant cis and trans deoxyschizandrins were performed using high resolution NMR and molecular models.

Intramolecular Oxidative Coupling of Aromatic Compounds. V. para-para Diphenolic Oxidative Coupling as a Possible Route to the Eupodienone Skeleton

The synthesis of (2RS,3RS)-1,4-bis(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dimethylbutan-1-one (9) is described.Diphenolic oxidative coupling of (9) gave the unstable dienone (24), which decomposed in methanol to give what is believed to be the acetal (26).Syn

Intramolecular Oxidative Coupling of Aromatic Compounds. IV. Oxidation of Non-Phenolic Substrates

Intramolecular non-phenolic coupling of (2RS,3SR)-1,4-bis(4-benzyloxy-3,5-dimethoxyphenyl)-2,3-dimethylbutan-1-one (6) failed.Oxidation of the derived butane (9) gave the aryltetralin (14) in low yield.

Syntheses of (+/-)-Deoxyschizandrin and the Lignan, 1,4-Bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane

(+/-)-Deoxyschizandrin (1) has been synthesised through a dimerisation reaction as a key step.The Grignard reagent from 1-(3,4,5-trimethoxyphenyl)-2-bromopropane (10) on reaction with 2-t-butyl-3-phenyloxaziridine gives 1,4-bis(3,4,5-trimethoxyphenyl)-2,3-dimethylbutane (11), which is cyclised using vanadium oxytrifluoride to get deoxyschizandrin (1).Following the above methodology, 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane (2), a lignan has also been prepared.

SYNTHESIS OF DIARYLBUTANES FROM CORDIGERINES AND REINVESTIGATION OF THEIR OXIDATIVE COUPLINGS IN DEOXYSCHIZANDRINS. - AN UNUSUAL FORMATION OF PHENYLTETRALIN LIGNANS -

Dibenzylbutanolide lignans including cordigerines were synthetized and transformed in the corresponding diarylbutane lignans which were submitted to non-phenolic oxidative coupling conditions by using RuO2 or Tl2O3 in trifluoroacetic medium to give deoxyschizandrins.A concurently aryl-benzyl coupling leads to the formation of the corresponding phenyltetralin of which the structure was confirmed by total synthesis.