144539-74-2

Upstream product

• 120-57-0 piperonal 
• 72430-92-3 4-[(3,4-dimethoxyphenyl)methyl]dihydrofuran-2-one 
• 115061-18-2 (E)-3-(methoxycarbonyl)-4-(3,4-dimethoxyphe-nyl)but-3-enoic acid 
• 78647-52-6 (+/-)-4-(3,4-dimethoxyphenyl)-3-methoxycarbonylbutanoic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 78647-51-5 4-[3,4-dimethoxyphenyl]-3-(methoxycarbonyl)-3-butenoic acid 
• 60354-22-5 4-[Bis(phenylsulfanyl)methyl]-1,2-dimethoxybenzene 
• 103844-12-8 erythro-3-<3'',4''-dimethoxy-α,α-bis(phenylthio)benzyl>-2-(α-hydroxy-3',4'-methylenedioxybenzyl)-γ-butyrolactone 

Downstream Products

• 72622-61-8 α-(trans-3',4'-methylenedioxybenzylidene)-β-(3,4-dimethoxybenzyl)-γ-butyrolactone 
• 18884-25-8 (3R^*,4R^*)-3-<3,4-(methylenedioxy)benzyl>-4-(3,4-dimethoxybenzyl)-γ-butyrolactone 
• 131318-40-6 (3S^*,4R^*)-3-methyl-3-<3,4-(methylenedioxy)benzyl>-4-(3,4-dimethoxybenzyl)-γ-butyrolactone 

Relevant academic research and scientific papers

Simple synthesis of trans-α,β-dibenzyl-γ-butyrolactone lignans by diastereoselective reduction of α-benzylidene-β-benzyl-γ-butyralactones using NaBH4-NiCl2

trans-α,β-Dibenzyl-γ-butyrolactone lignans were synthesized by stereoselective reduction of α-benzylidene-β-benzyl-γ-butyrolactones using NaBH4-NiCl2. The reduction is found to proceed via conjugate addition of a hydride to an α-benz

Stereoselective syntheses of cis- and trans-isomers of α-hydroxy-α,β-dibenzyl-γ-butyrolactone lignans: New syntheses of (±)-trachelogenin and (±)-guayadequiol

Cis- and trans-isomers of α-hydroxy-α,β-dibenzyl-γ-butyrolactone lignans 1a,d-g and 2a,c,d were stereoselectively synthesized in good yields based on the electrophilic addition to the metal enolate of α-benzyl-γ-butyrolactone derivatives 1l-o and 3 as a key step. This method was applied to the syntheses of (±)-trachelogenin and (±)-guayadequiol, representative examples of the trans- and cis-isomers of α-hydroxy-α,β-dibenzyl-γ-butyrolactone lignan series.

SYNTHESIS OF LIGNANS RELATED TO THE PODOPHYLLOTOXIN SERIES

The dibenzyl-γ-butyrolactone derivative (6), readily prepared by tandem conjugate addition to but-2-en-4-olide, undergoes cyclisation with trifluoroacetic acid to afford retrochinensin (10).After desulphurisation of (6) with Raney nickel, cyclisation yields the aryltetralin lactone (9).Treatment of (6) with concentrated perchloric acid gives a quantitative yield of the rearranged compound (11), which after appropriate modification can be cyclised to afford either the retro-dihydroarylnaphthalene lactone (13), or the 4-substituted aryltetralin lactone (15).Extension of this approach to a second dibenzylbutyrolactone derivative (21) leads to the retro-dihydroarylnaphthalene lactone (25), but gives only a low yield of the required podophyllotoxin derivative (27).

Synthesis of Aryltetralin and Dibenzylbutyrolactone Lignans: (+/-)-Lintetralin, (+/-)-Phyltetralin, and (+/-)-Kusunokinin

Application of a general synthetic pathway for aryltetralin and dibenzylbutyrolactone lignans, starting from the lithium enolate of 3-(3,4-dimethoxybenzyl)butyrolactone (1) led to syntheses of (+/-)-lintetralin (4), (+/-)-phyltetralin (5), (+/-)-isogalcat

STRUCTURE AND SYNTHESYS OF HYPOPHYLLANTHIN, NIRTETRALIN, PHYLTETRALIN AND LINTETRALIN

Structures propounded for the four aryltetralin lignan constituents isolated from Phyllanthus niruri Linn. are confirmed by syntheses of their (+/-)-forms.