118917-45-6

Upstream product

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

Downstream Products

• 72622-61-8 α-(trans-3',4'-methylenedioxybenzylidene)-β-(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

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

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).

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.