6258-32-8

Upstream product

• 6259-84-3 (E)-3-(benzo[d][1,3]dioxol-5-yl)allyl 3-(3,4,5-trimethoxyphenyl)propiolate 
• 137047-03-1 trans-4-(2-Bromo-4,5-methylenedioxybenzyl)-3-(α-chloro-3,4,5-trimethoxybenzyl)dihydro-2(3H)-furanone 
• 137047-04-2 (Z)-4-(2-Bromo-4,5-methylenedioxybenzyl)-3-(3,4,5-trimethoxybenzylidene)dihydro-2(3H)-furanone 

Downstream Products

• 6258-41-9 5-(3,4,5-Trimethoxy-phenyl)-8H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 
• 477-51-0 (+/-)-Isopicrodesoxypodophyllotoxin 
• 133906-63-5 (+/-)-2-Hydroxymethyl-6,7-methylenedioxy-4-(3',4',5'-trimethoxyphenyl)-1,2-dihydro-3-naphthoic acid 
• 1254-07-5 7-Hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 477-51-0 (5S,5aS,8aR)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3′,4’:6,7]naphtho[2,3-d][1,3]-dioxol-6(5aH)-one 

Relevant academic research and scientific papers

Synthesis and Computational Studies Demonstrate the Utility of an Intramolecular Styryl Diels-Alder Reaction and Di-t-butylhydroxytoluene Assisted [1,3]-Shift to Construct Anticancer dl-Deoxypodophyllotoxin

Deoxypodophyllotoxin is a secondary metabolite lignan possessing potent anticancer activity with potential as a precursor for known anticancer drugs, but its use is limited by scarcity from natural sources. We here report the total synthesis of racemic de

Synthesis of podophyllotoxin derivatives by means of tributyltin hydride- or palladium-mediated cyclization of α-benzylidene-β-(o-bromobenzyl)-γ-lactones

Synthesis of podophyllotoxin derivatives based on an aryl radical cyclization of α-benzylidene-β-(o-bromobenzyl)-γ-lactones 20 and 21 has been examined. Treatment of a mixture of the alcohols 18a and 18b (ca. 1:1), prepared from 6-bromopiperonal (10) in 7 steps, with methanesulfonyl chloride gave a ca. 3:1 mixture of the chlorides 19a and 19b, which was treated with DBU to give the (Z)-and (E)-α-benzylidene-γ-lactones 20 and 21 in 64 and 22% yields, respectively. Thermolysis of the mixture of the sulfoxides 23a and 23b, prepared from 18a,b, afforded the E-isomer 21 as a major product. The Z-benzylidenelactone 20 when treated with Bu3SnH in the presence of AlBN gave the 6-endo-trig radical cyclization product, (±)-deoxyisopicropodophyllin (24), and the 5-exo-trig cyclization product 25 in 29 and 49% yields, respectively. The E-isomer 21, however, gave only the 5-exo cyclization product 25. On the other hand, treatment of 20 with PdCl2(PPh3)3 gave (±)-γ-apopicropodophyllin (29) in 75% yield. Similar treatment of 21 afforded no cyclization product, but, in the presence of sodium formate (H- source), gave the 5-exo cyclization product 25 in 84% yield.

SYNTHETIC STUDIES ON PODOPHYLLUM LIGNANS: TRIBUTYLTIN HYDRIDE-INDUCED RADICAL CYCLIZATION AND INTRAMOLECULAR HECK REACTION OF α-BENZYLIDENE-β-(o-BROMOBENZYL)-γ-LACTONES

Tributyltin hydride-induced radical cyclization of the (Z)-α-benzylidene-β-(o-bromobenzyl)-γ-lactone (16) gave the 6-endo cyclization product, (+/-)-deoxyisopicropodophyllin (18), and the 5-exo cyclization product (19).On the other hand, the intramolecular Heck reaction of 16 provided (+/-)-γ-apopicropodophyllin (20) as a sole cyclization product.