47539-89-9

Upstream product

• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 54-04-6 mescaline 
• 10313-60-7 3,4-dimethoxyphenylacetyl chloride 
• 2103-57-3 2,3,4-trimethoxybenzaldehyde 
• 118474-94-5 (E)-1-nitro-2-(2',3',4'-trimethoxyphenyl)ethene 
• 3937-16-4 2-(2,3,4-trimethoxyphenyl)ethylamine 
• 24237-31-8 N-<2-(2,3,4-trimethoxyphenyl)ethyl>-2-(3,4-dimethoxyphenyl)acetamide 

Downstream Products

• 919082-31-8 ethyl 1-(3,4-dimethoxyphenyl)-2-(2,4-dibenzyloxy-5-methoxyphenyl)-7,8,9-trimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate 
• 919082-44-3 14-(3,4-dimethoxyphenyl)-3-acetoxy-2,10,11,12-tetramethoxy-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 149355-75-9 14-(3,4-dimethoxyphenyl)-3-hydroxy-2,10,11,12-tetramethoxy-8,9-dihydro-6H-chromeno[4’,3’:4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 187156-50-9 14-(3,4-dimethoxyphenyl)-3-acetoxy-2,10,11,12-tetramethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 1027195-13-6 2-(2,4-diisopropoxy-5-methoxy-phenyl)-1-(3,4-dimethoxy-phenyl)-7,8,9-trimethoxy-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-3-carboxylic acid ethyl ester 
• 363134-17-2 1-(3,4-dimethoxy-benzyl)-5,6,7-trimethoxy-3,4-dihydro-isoquinoline 2-oxide 
• 32039-37-5 1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-5,6,7-trimethoxyisoquinoline 

Relevant academic research and scientific papers

Total synthesis of natural and unnatural lamellarins with saturated and unsaturated D-rings

(Chemical Equation Presented) Twenty-eight natural and unnatural lamellarins with either a saturated or an unsaturated D-ring were synthesized according to our developed synthetic route. The key step involved the Michael addition/ring closure (Mi-RC) of the benzyldihydroisoquinoline and α-nitrocinnamate derivatives, which provided the 2-carboethoxypyrrole intermediates in moderate to good yields (up to 78% yield). Subsequent hydrogenolysis/lactonization furnished lamellarins with a saturated D-ring in excellent yields (up to 93% yield). DDQ oxidation of the saturated lamellarin acetates led directly to the corresponding unsaturated analogues in 54-95% yield. In addition, only two steps in our developed strategy require column chromatography.

Synthesis of (±)-Glaucine and (±)-Neospirodienone via an One-Pot Bischler-Napieralski Reaction and Oxidative Coupling by a Hypervalent Iodine Reagent

Condensation of 3,4-dimethoxybenzeneethanamine (3d) and various benzeneacetic acids, i.e., 4a-e, via a practical and efficient one-pot Bischler-Napieralski reaction, followed by NaBH4 reduction, produced a series of 1-benzyl-1,2,3,4-tetrahydroisoquinolines, i.e., 5a-e, in satisfactory yields (Scheme 3). Oxidative coupling of the N-acyl and N-methyl derivatives 6a-e of the latter with hypervalent iodine ([IPh(CF 3COO)2]) yielded products with two different skeletons (Scheme 4). The major products from N-acyl derivatives 6a-c were (±)-N-acylneospirodienones 2a-c, while the minor was the 3,4-dihydroisoquinoline 7. (±)-Glaucine (1), however, was the major product starting from N-methyl derivative 6e. Possible reaction mechanisms for the formation of these two types of skeleton are proposed (Scheme 5).