118825-99-3

Upstream product

• 6302-93-8 5-[Bis(phenylsulfanyl)methyl]-1,3-benzodioxole 
• 497-23-4 2-buten-4-olide 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 108-98-5 thiophenol 
• 103844-12-8 erythro-3-<3'',4''-dimethoxy-α,α-bis(phenylthio)benzyl>-2-(α-hydroxy-3',4'-methylenedioxybenzyl)-γ-butyrolactone 
• 120-57-0 piperonal 

Downstream Products

• 118826-02-1 3-(α-benzoyloxy-3'',4''-methylenedioxybenzyl)-2-(3',4',5'-trimethoxy-α-phenylthiobenzyl)-γ-butyrolactone 
• 118826-04-3 Benzoic acid (S)-benzo[1,3]dioxol-5-yl-{(3R,4S)-4-[(S)-methoxy-(3,4,5-trimethoxy-phenyl)-methyl]-5-oxo-tetrahydro-furan-3-yl}-methyl ester 
• 118826-05-4 3-(α-benzoyloxy-3'',4''-methylenedioxybenzyl)-2-(α-hydroxy-3',4',5'-trimethoxybenzyl)-γ-butyrolactone 
• 6274-07-3 4-benzoyloxy-3-hydroxymethyl-6,7-methylenedioxy-1-(3',4',5'-trimethoxyphenyl)-1,2,3,4-tetrahydro-2-naphthoic acid γ-lactone 
• 118826-01-0 3-(α-hydroxy-3'',4''-methylenedioxybenzyl)-2-(3',4',5'-trimethoxy-α-phenylthiobenzyl)-γ-butyrolactone 
• 118826-00-9 3-(3'',4''-methylenedioxybenzoyl)-2-(3',4',5'-trimethoxy-α-phenylthiobenzyl)-γ-butyrolactone 

Relevant academic research and scientific papers

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).