98678-45-6

Upstream product

• 186581-53-3 diazomethane 
• 108-31-6 maleic anhydride 
• 67-56-1 methanol 
• 98678-36-5 trans-1-acethoxy-3-phenyl-1,3-dihydrobenzothiophene 2,2-dioxide 
• 104638-02-0 (1R,2S,3R,4R)-1-Phenyl-4-(1-phenyl-ethoxy)-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester 
• 32832-95-4 2-benzylbenzaldehyde 
• 98678-35-4 cis-1-acethoxy-3-phenyl-1,3-dihydrobenzothiophene 2,2-dioxide 
• 624-49-7 dimethylfumarate 
• 104638-01-9 (1R,2S,3R,4R)-1-Phenyl-4-(1,2,2-trimethyl-propoxy)-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester 
• 104703-76-6 Acetic acid (3aR,4R,9R,9aR)-1,3-dioxo-9-phenyl-1,3,3a,4,9,9a-hexahydro-naphtho[2,3-c]furan-4-yl ester 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 98678-43-4 (1R,2R,3R,4R)-1-Acetoxy-4-phenyl-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester 
• 112396-00-6 1-benzylthio-1,3-dihydrobenzothiophene 2,2-dioxide 
• 112395-94-5 (1R,2S,3S,4R)-1-Benzylsulfanyl-4-phenyl-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester 

Downstream Products

• 98678-40-1 2,3-bis(methoxycarbonyl)-1-phenyl-1,2,3,4-tetrahydronaphthalene 
• 98678-39-8 methyl 3-(methoxycarbonyl)-1-phenyl-1,2,3,4-tetrahydro-naphthalene-2-carboxylate 

Relevant academic research and scientific papers

Diels-Alder Additions to 1-Phenyl-2-benzopyran-3-one and Transformations of the Adducts: Model Experiments for Podophyllotoxin Synthesis

1-Phenyl-2-benzopyran-3-one 2 adds to a series of unsymmetrically substituted dienophiles (methyl acrylate, ethyl crotonate, methyl ω-bromocrotonate, and crotonaldehyde) with regioselectivity largely determined by the phenyl group but with little endo-exo

Synthesis of (+/-)-4-Deoxypodophyllotoxin, (+/-)-Podophyllotoxin and (+/-)-Epipodophyllotoxin

6,7-Methylenedioxy-1-(3',4',5'-trimethoxyphenyl)-2-benzopyran-3-one 1 and dimethyl fumarate in acetonitrile give mostly the C-2 exo-CO2Me adduct 4 which is transformed in four steps into epipodophyllotoxin 10a.Attempted addition of dimethyl maleate to 1 p

Regioselective Suprafacial 1,5-Hydrogen Shifts in o-Quinodimethanes; a Route to 4-Deoxypodophyllotoxin

The o-quinodimethane intermediate (4a) with cis-CO2Me groups undergoes regioselective 1,5-hydrogen shift to the cis-dihydronaphthalene (5a) whilst its trans-isomer (9a) gives both 1,5-hydrogen shift products (6a) and (7a); (5a) is readily converted into 4

Preparation of 1-thio and 1-amino substituted 1,3-dihydrobenzothiophene 2,2-dioxides

The 1-hydroxy substituent in 1-hydroxy-1,3-dihydrobenzothiophene 2,2-dioxides is readily replaced by alkoxy, alkylthio, and amino groups.These compounds serve as precursors of alkoxy, alkylthio, and amino substituted o-quinodimethanes.Cycloaddition rea

E,E- and E,Z-α-phenyl-α'-acetoxyorthoquinodimethane: steric and electronic control of cycloaddition reactions

E,E- and E,Z-α-phenyl-α'-acetoxyorthoquinodimethanes have been prepared from the corresponding cis- and trans-1-acetoxy-3-phenyl-1,3-dihydrobenzothiophene-2,2-dioxides.The regio- and diastereoselectivity of the addition reactions with dimethyl fumarate, dimethyl maleate, maleic anhydride, and methyl crotonate have been determined.Ab initio calculations have been carried out on orthoquinodimethane and its α-phenyl and α-oxy derivatives.A correlation has been made between the steric and electronic properties of the orthoquinodimethanes and the regio- and diastereoselectivity of their Diels-Alder reactions.

Diastereoselectivity and asymmetric induction in the Diels-Alder reaction of o-quinodimethanes

The extent of asymmetric induction in the bimolecular Diels-Alder reactions of chiral o-quinodimethanes with dimethyl fumarate, methyl acrylate, and maleic anhydride has been studied. o-Quinodimethanes with chiral α-alkoxy groups were prepared from 1-alko

Stereoselectivity in the Diels-Alder Reaction of Phenyl- and Oxy-Substituted o-Quinodimethanes

Phenyl-, methoxy-, and acetoxy-substituted o-quinodimethanes (o-QDM) have been added to dimethyl fumarate and maleate to determine the stereoselectivity of the addition reaction.The o-QDM's were generated from the corresponding 1,3-dihydrobenzothiophen