88176-89-0

Upstream product

• 88176-87-8 C₂₀H₂₅NO₅ 
• 80245-51-8 4-lithio-1,2-dimethoxybenzene 
• 88176-85-6 3-(3,4-dimethoxyphenyl)-3-(2-methyl-2-propenyl)-1,4-cyclohexanedione 1-(ethylene acetal) 
• 88176-86-7 3a-(3,4-dimethoxyphenyl)-5,5-(ethylenedioxy)-3,3a,4,5,6,7-hexahydro-2H-inden-2-one 
• 88176-84-5 3-(3,4-dimethoxyphenyl)-1,4-cyclohexanedione-1-(ethylene acetal) 
• 88176-83-4 3-(3,4-dimethoxyphenyl)-3-cyclohexenone ethylene acetal 
• 91713-15-4 3a-(3,4-dimethoxyphenyl)-5,5-(ethylenedioxy)-3,3a,4,5,6,7-hexahydro-2H-inden-2-one N-methylnitrone 
• 91713-14-3 7-(3,4-Dimethoxy-phenyl)-7-(2-oxo-propyl)-1,4-dioxa-spiro[4.5]decan-8-one 
• 91713-13-2 7-(3,4-Dimethoxy-phenyl)-1,4-dioxa-spiro[4.5]decan-8-ol 
• 2859-78-1 4-Bromoveratrole 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 20036-53-7 3-<3,4-(dimethoxy)phenyl>-2-cyclohexen-1-one 
• 88176-88-9 4a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2-methyl-3-oxo-2,3,4,4a,5,6,7,8-octahydroisoquinoline 

Downstream Products

• 88176-91-4 cis-4a-(3,4-dimethoxyphenyl)-2-methyl-6-oxo-3,4,4a,5,6,7,8,8a-octahydroisoquinolinium perchlorate 

Relevant academic research and scientific papers

A New Approach to Morphinans: Total Synthesis of O-Methylpallidinine

We have devised a general method for the synthesis of 4a-aryloctahydroisoquinolines related to morphine and have shown how these compounds may be used in a route to morphinan alkaloids.The key step in this route involves the addition of diazomethane to a 4a-aryloctahydroisoquinolinium salt, followed by spontaneous cyclization to the morphinan.Studies of this step indicate that it is not compatible with the presence of an alkoxyl group at C4 of the aryl ring.The value of this method has been demonstrated in the context of stereospecific total synthesis of O-methylpallidinine.

TOTAL SYNTHESIS OF O-METHYLPALLIDININE

O-Methylpallidinine, a recently isolated morphinan alkaloid, has been synthesized in 16 steps from 1,4-cyclohexanedione and 3-bromoveratrole.The synthesis employs a new method for preparing the mophinan skeleton in which diazomethane is added to an aryloc