119030-66-9

Upstream product

• 1432494-09-1 (E)-ethyl 4-(3',4'-dimethoxyphenyl)but-2-enoate 
• 28028-62-8 ethyl ferulate 
• 5703-21-9 3,4-dimethoxyphenylacetaldehyde 
• 54844-36-9 3-(3,4-dimethoxyphenyl)propane-1,2-diol 
• 105245-81-6 3-(4-benzyloxy-3-methoxyphenyl)propionic acid chloride 
• 30034-49-2 β-(4-benzyloxy-3-methoxyphenyl)propionic acid 
• 186895-24-9 ethyl 3-(4-(benzyloxy)-3-methoxy)propanoate 
• 61292-90-8 ethyl 3-(4-hydroxy-3-methoxyphenyl)propanoate 
• 93-15-2 1,2-dimethoxy-4-(2-propenyl)benzene 
• 123195-63-1 4-benzyloxy-3-methoxybenzaldehyde-bis-phenylthioacetal 
• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 580-72-3 (2RS,3RS)-2,3-bis-(4-hydroxy-3-methoxybenzyl)butyrolactone 
• 67-68-5 dimethyl sulfoxide 

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.

FORMATION OF (-)-ARCTIGENIN IN FORSYTHIA INTERMEDIA

Forsythia intermedia cell-free extracts were examined for their ability to catalyse the enantioselective and regiospecific O-methylation of matairesinol.In contrast to the enzymatic steps defined from (+)-pinoresinol to (-)-matairesinol, the conversion of matairesinol into arctigenin was not highly enenatioselective; both (+)- and (-)-antipodes of matairesinol served as substrates for methylation, with the naturally occuring (-)-enantiomer slightly preferred.But the cell-free extracts also catalyses the synthesis of (+)- and (-)-isoarctigenins, with (-)-matairesinol again the preferred substrate.Thus the O-methylation of matairesinol, catalysed by F. intermedia cell-free extracts, is neither highly enantioselective nor regiospecific.No evidence that subsequent methylation of either arctigenin or isoarctigenin occured to afford dimethyl matairesinol was obtained, i.e. the O-methyltransferase(s) only catalysed monomethylation.Taken together, it is proposed that post-coupling methylation does not proceed via regiospecific methylation of matairesinol to give arctigenin directly.Instead, regiospecific glucosylation first occurs to afford matairesinoside; subsequent methylation affords arctiin, which is then converted into arctigenin via action of a β-glucosidase. Key Word Index - Forsythia; Oleaceae; O-methyltransferases; glucosyltransferases; lignans; neolignans; biosynthesis; enantioselectivity; regiospecifity; chiral separation.

Oxidative Coupling of Lignans. IV. Monophenolic Oxidative Coupling

Oxidative coupling of the monophenolic monoester (6) gives an aryltetralin (12) which is a potential intermediate for the synthesis of clinically active monophenolic lignan lactones.In contrast, oxidative couplings of the monophenols (32) and (35), derived from matairesinol (29), give mixtures of diastereoisomeric cyclooctadiene lignans while 4'-demethyldeoxypodorhizon (26) does not cyclize.These results show that the degree of aromatic substitution in monophenolic diarylbutanes plays an important role in determining the outcome of oxidative coupling.An alternative synthesis of the lactone (57) from piperonal has been investigated.