137047-03-1

Basic information

• Product Name: threo-trans-4-(2-Bromo-4,5-methylenedioxybenzyl)-3-(α-chloro-3,4,5-trimethoxybenzyl)dihydro-2(3H)-furanone
• CAS NO: 137047-03-1
• Molecular Weight: 513.769
• Mol File: 137047-03-1.mol

Chemical Properties

• CAS DataBase Reference: threo-trans-4-(2-Bromo-4,5-methylenedioxybenzyl)-3-(α-chloro-3,4,5-trimethoxybenzyl)dihydro-2(3H)-furanone(CAS DataBase Reference)
• NIST Chemistry Reference: threo-trans-4-(2-Bromo-4,5-methylenedioxybenzyl)-3-(α-chloro-3,4,5-trimethoxybenzyl)dihydro-2(3H)-furanone(137047-03-1)
• EPA Substance Registry System: threo-trans-4-(2-Bromo-4,5-methylenedioxybenzyl)-3-(α-chloro-3,4,5-trimethoxybenzyl)dihydro-2(3H)-furanone(137047-03-1)

Safety Data

• Hazardous Substances Data: 137047-03-1(Hazardous Substances Data)

Upstream product

• 137047-01-9 4-<2-Bromo-4,5-methylenedioxy-α-cyano-α-(1-ethoxyethoxy)benzyl>dihydro-2(3H)-furanone 
• 137047-02-0 4-(2-Bromo-4,5-methylenedioxybenzyl)dihydro-2(3H)-furanone 
• 137046-98-1 (6-Bromo-benzo[1,3]dioxol-5-yl)-trimethylsilanyloxy-acetonitrile 
• 137046-99-2 (6-Bromo-benzo[1,3]dioxol-5-yl)-hydroxy-acetonitrile 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 120-57-0 piperonal 
• 137046-97-0 trans-4-(2-Bromo-4,5-methylenedioxybenzyl)-3-(3,4,5-trimethoxy-α-hydroxybenzyl)dihydro-2(3H)-furanone 
• 137047-00-8 2-(2-Bromo-4,5-methylenedioxyphenyl)-2-(1-ethoxyethoxy)acetonitrile 
• 137046-96-9 4-(2-Bromo-4,5-methylenedioxybenzoyl)dihydro-2(3H)-furanone 

Downstream Products

• 477-51-0 (+/-)-Isopicrodesoxypodophyllotoxin 
• 6258-32-8 (dl)-5-(3,4,5-trimethoxyphenyl)-8a,9-dihydrofuro[3′,4’:6,7]-naphtho[2,3-d][1,3]dioxol-6(8H)-one 
• 150422-66-5 4b,7,7a,8-Tetrahydro-4b-(3,4,5-trimethoxybenzyl)-5H-furo<3',4':1,2>indeno<5,6-d>-1,3-dioxol-5-one 
• 137047-05-3 (E)-4-(2-Bromo-4,5-methylenedioxybenzyl)-3-(3,4,5-trimethoxybenzylidene)dihydro-2(3H)-furanone 
• 137047-04-2 (Z)-4-(2-Bromo-4,5-methylenedioxybenzyl)-3-(3,4,5-trimethoxybenzylidene)dihydro-2(3H)-furanone 

Relevant articles and documents

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.