111266-00-3

Basic information

• Product Name: 2(3H)-Furanone, dihydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-, (R)-
• CAS NO: 111266-00-3
• Molecular Formula: C12H14O4
• Molecular Weight: 222.241
• Mol File: 111266-00-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2(3H)-Furanone, dihydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Furanone, dihydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-, (R)-(111266-00-3)
• EPA Substance Registry System: 2(3H)-Furanone, dihydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-, (R)-(111266-00-3)

Safety Data

• Hazardous Substances Data: 111266-00-3(Hazardous Substances Data)

Upstream product

• 92831-74-8 4-<<4-(benzyloxy)-3-methoxyphenyl>methyl>dihydro-2(3H)-furanone 
• 111265-99-7 C₁₃H₁₄O₆^(2-)*2K⁽¹⁺⁾ 
• 111265-97-5 (R)-(+)-methyl α-vanillylhemisuccinate 

Downstream Products

• 518-55-8 conidendrin 
• 127951-04-6 (2R,3R)-(6R,S)-(+)-2-(4-Benzyloxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 127951-05-7 (2R,3R)-(6R,S)-(+)-2-(4-Hydroxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 127951-03-5 (3R)-(6R,S)-(+)-3-(α-Benzyloxy-4-trimethylsiloxy-3-methoxybenzyl)butan-4-olide 
• 127951-01-3 (3R)-(6R,S)-(+)-3-(α-Benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide 
• 140193-27-7 (-)-O-6-Benzyl-α-conidendrine 
• 25047-22-7 (-)-O-Diacetyl-α-conidendrine 
• 127951-01-3 (R)-4-[(S)-Benzyloxy-(4-hydroxy-3-methoxy-phenyl)-methyl]-dihydro-furan-2-one 
• 127951-02-4 (R)-4-[(R)-Benzyloxy-(4-hydroxy-3-methoxy-phenyl)-methyl]-dihydro-furan-2-one 
• 580-72-3 matairesinol 
• 29388-33-8 (3R,4R)-3,4-bis(4-hydroxy-3-methoxybenzyl)-4-butanolide 
• 111194-07-1 (3R,4R)-3,4-bis(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one 
• 111194-10-6 O-dibenzylretrodendrin 
• 939963-12-9 (3S,4R)-4-(4-Benzyloxy-3-methoxy-benzyl)-3-[(4-benzyloxy-3-methoxy-phenyl)-hydroxy-methyl]-dihydro-furan-2-one 

Relevant articles and documents

Intramolecular regioselective insertion into unactivated prochiral carbon-hydrogen bonds with diazoacetates of primary alcohols catalyzed by chiral dirhodium(II) carboxamidates. Highly enantioselective total synthesis of natural lignan lactones

Intramolecular insertion into unactivated prochiral C-H bonds of 3-aryl-1-propyl diazoacetates catalyzed by dirhodium(II) tetrakis[methyl 1-(3-phenyl propanoyl)imidazolidin-2-one-4(R or S)-carboxylate], Rh2(4R-MPPIM)4 or Rh2(4S-MPPIM)4, occurs in 91-96% ee and with virtually complete regiocontrol for the formation of β-benzyl-γ-butyrolactones. This methodology has been applied to the total synthesis of dibenzylbutyrolactone lignans (-)- and (+)-enterolactone, (-)- and (+)-hinokinin, and (+)-arctigenin from substituted cinnamic acids in 19-27% overall yields. Aryltetralin lignan (+)-isodeoxypodophyllotoxin was prepared from the reactant 3,4-(methylenedioxy)cinnamic acid in 36% yield overall, and the lactone precursor to (+)-isolauricerisinol was formed in 96.5% ee and 23% yield overall. Applications of the chiral Rh2(MPPIM)4 catalysts to fully aliphatic systems resulting in the formation of β-substituted-γ-butyrolactones with high regiocontrol and with 93-96% ee have demonstrated the generality of this methodology. A model that provides accurate predictions of β-substituted-γ-butyrolactone absolute configurations in these asymmetric metal carbene transformations is described.

THE SYNTHESES OF (R)-(+)-β-VANILLYL-γ-BUTYROLACTONE AND OF CHIRAL LIGNANS THEREFROM

(R)-(+)-β-vanillyl-γ-butyrolactone was obtained in 4 steps including a resolution, from vanillin and dimethyl succinate, and was used for the total syntheses of 5 naturally occurring and optically active lignans such as (+)-isolariciresinol 20.