118535-07-2

Upstream product

• 7306-46-9 4-chloromethyl-1,2-dimethoxy-benzene 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 120-57-0 piperonal 
• 497-23-4 2-buten-4-olide 
• 83318-94-9 (3,4-dimethoxybenzyl)(phenyl)sulfane 

Downstream Products

• 103844-19-5 3-hydroxymethyl-6,7-dimethoxy-1-(3',4'-methylenedioxyphenyl)-4α-phenylthio-1,2,3,4-tetrahydro-2-naphthoic acid γ-lactone 
• 103844-19-5 3-hydroxymethyl-6,7-dimethoxy-1-(3',4'-methylenedioxyphenyl)-4β-phenylthio-1,2,3,4-tetrahydro-2-naphthoic acid γ-lactone 
• 103844-18-4 4-(3',4'-dimethoxyphenyl)-3-hydroxymethyl-6,7-methylenedioxy-3,4-dihydro-2-naphthoic acid γ-lactone 

Relevant academic research and scientific papers

A SHORT VERSATILE SYNTHESIS OF ARYLTETRALIN LIGNANS INCLUDING DEOXYISOPODOPHYLLOTOXIN AND EPI-ISOPODOPHYLLOTOXIN

Cyclisation of tandem conjugate addition products (10), (15), and (20), prepared by reaction of anions derived from benzyl phenyl and benzyl t-butyl sulphides with but-2-en-4-olide, affords a series of aryltetralin lignans belonging to either the 'normal' or the 'retro' lactone series.Desulphurisation of compound (15) followed by cyclisation, or desulphurisation of the cyclised product (22b), affords deoxyisopodophyllotoxin (5), while treatment of compound (22b) with mercury(II) trifluoroacetate yields epi-isopodophyllotoxin (6).

SYNTHESIS OF DEOXYISOPODOPHYLLOTOXIN AND EPIISOPODOPHYLLOTOXIN.

Cyclisation of the tandem conjugate addition products 1-3 by displacement of either the OH or SPh group provides a short efficient synthesis of lignan lactones including compounds of the clinically important podophyllotoxin series.