103844-22-0

Upstream product

• 71616-31-4 (E)-3,4-methylenedioxycinnamyl (Z)-3-(3,4,5-trimethoxyphenyl)acrylate 
• 7460-41-5 (E)-3,4-methylenedioxycinnamyl (E)-3-(3,4,5-trimethoxyphenyl)acrylate 
• 172271-46-4 (Z)-3,4-methylenedioxycinnamyl (E)-3-(3,4,5-trimethoxyphenyl)acrylate 
• 103844-20-8 3-hydroxymethyl-5,6,7-trimethoxy-4-(3',4'-methylenedioxyphenyl)-1α-phenylthio-1,2,3,4-tetrahydro-2-naphthoic acid γ-lactone 

Relevant academic research and scientific papers

A new synthesis of podophyllum lignans by Weitz' aminium salt-induced free radical cycloaddition reaction of a doubly unsaturated ester

(±)-Isopodophyllotoxin (1e) and related lactones 12, 13, 14 were synthesized by a biomimetic procedure from the doubly unsaturated esters 11a and 11b by means of an oxidative free radical cycloaddition reaction utilizing a stable cation radical salt, Weitz' aminium salt, in one step. (±)-Isopicropodophyllin (1g), the trans-fused lactones, 12, 13, and 16, and the cis-fused lactone 17 were also synthesized from the esters 11c and 11d by the reaction with the same reagent.

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).