Anodic oxidation of phenolic compounds. Part 5. Anodic methoxylation of phenols. A simple synthesis of quinones, quinone acetals, and 4-methyl-α-methoxycyclohexa-2,5-dienones

1978 ◽  
pp. 696-707 ◽  
Author(s):  
Anders Nilsson ◽  
Ulf Palmquist ◽  
Tore Pettersson ◽  
Alvin Ronlán
Keyword(s):  
Phenolic Compounds ◽  
Anodic Oxidation ◽  
Simple Synthesis ◽  
Anodic Methoxylation

Anodic oxidation pathways of phenolic compounds

1972 ◽  
Vol 38 (2) ◽  
pp. 389-395 ◽  
Author(s):  
L. Papouchado ◽  
G. Petrie ◽  
R.N. Adams
Keyword(s):  
Phenolic Compounds ◽  
Anodic Oxidation

Sedum alkaloids. XI. Synthesis of sedinone and sedacrine by application of anodic oxidation

1991 ◽  
Vol 69 (2) ◽  
pp. 211-217 ◽  
Author(s):  
Frank Driessens ◽  
ClaUDE Hootelé
Keyword(s):  
Nucleophilic Substitution ◽  
Key Words ◽  
Anodic Oxidation ◽  
Methoxy Group ◽  
High Yield ◽  
Piperidine Alkaloids ◽  
Piperidine Derivative ◽  
Sedum Acre ◽  
Anodic Methoxylation

α-Methoxycarbamate 12, synthetic precursor of the 2,6-disubstituted alkaloids of Sedum acre, was obtained in high yield from 2-phenacylpiperidine 5; the key step of the synthesis rests on the anodic methoxylation, which allows the functionalization of carbon 6. Nucleophilic substitution of the methoxy group by an acetonyl chain leads, after the required transformations, to sedinone 23. Bromomethoxylation of the enecarbamate 19 followed by dehydrohalogenation and nucleophilic substitution of the methoxy group leads to sedacrine 33. In both cases, the nucleophilic substitution of the methoxy group leads to a cis 2,6-disubstituted piperidine derivative. Key words: synthesis, piperidine alkaloids, anodic methoxylation

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