157669-71-1

Upstream product

• 22231-61-4 2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine 
• 79-22-1 methyl chloroformate 
• 121-33-5 vanillin 
• 100-39-0 benzyl bromide 
• 63909-38-6 3-methoxy-4-benzyloxy-ω-nitrostyrolene 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 

Downstream Products

• 391609-26-0 6-acetoxy-6-methoxy-4-(2-methoxycarbonylamino-ethyl)-cyclohexa-2,4-dienone 
• 164228-27-7 2-(4-hydroxy-3-methoxyphenyl)-ethyl-N-methoxycarbonylamine 

Relevant academic research and scientific papers

Iodine (III)-mediated generation of nitrogen-tethered orthoquinol acetates for the construction of oxygenated indole, quinoline, and phenanthridine alkaloid motifs

Functionalized indole and quinoline derivatives are conveniently prepared from nitrogen-tethered 2-methoxyphenols via phenyliodine(III) diacetate mediated oxidative acetoxylation, followed by a fluoride- or base-induced intramolecular nucleophilic addition reaction. This regioselective Michael-type addition step is further discussed in view of the rearrangement of orthoquinol acetate intermediates into paraquinol acetates that is sometimes observed in situ. Application of this methodology to the synthesis of a functionalized phenanthridine, and its potential for the construction of polyoxygenated lycorine-type alkaloid skeleta are here described.

Synthesis of the salutaridine and aporphine skeleton via palladium(0) catalyzed cyclization and S(RN)1 reaction of 2'-bromoreticulines

The intramolecular aryl-aryl-coupling reactions of 2'-bromoreticulines are described. Their regioselectivity depends on the cyclization method. The palladium(0) catalyzed reaction of 22 leads preferentially to the salutaridine derivative 27, whilst via the photochemically induced S(RN)1 reaction of 22 the aporphine skeleton 24 is obtained.