189083-79-2

Upstream product

• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 64-69-7 Iodoacetic acid 
• 160257-85-2 5-iodo-2-methoxyphenol 
• 919082-37-4 ethyl 1-(3-benzyloxy-4-methoxyphenyl)-2-(2,4-dibenzyloxy-5-methoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate 
• 41183-13-5 1-(3-benzyloxy-4-methoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 5487-33-2 O-benzylhomoisovanillic acid 
• 54313-33-6 2-(3-(benzyloxy)-4-methoxyphenyl)acetyl chloride 
• 18028-10-9 N-(3-Benzyloxy-4-methoxy-phenyl)-N-(3,4-dimethoxy-phenaethyl)-acetamid 
• 1034028-91-5 (Z)-ethyl 2,4-bis(benzyloxy)-5-methoxy-α-nitrocinnamate 
• 621-59-0 isovanillin 
• 121-33-5 vanillin 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 

Downstream Products

• 596111-78-3 14-(3-acetoxy-4-methoxyphenyl)-3-acetoxy-2,11,12-trimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 475232-29-2 3-hydroxy-14-(3-hydroxy-4-methoxyphenyl)-2,11,12-trimethoxy-6H-[1]benzopyrano[4',3':4,5]-pyrrolo[2,1-a]isoquinolin-6-one 
• 919082-49-8 14-(3-acetoxy-4-methoxyphenyl)-3-acetoxy-2,11,12-trimethoxy-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 

Relevant academic research and scientific papers

Synthesis of lamellarin U and lamellarin G trimethyl ether by alkylation of a deprotonated α-aminonitrile

(Chemical Equation Presented) 1,2,3,4-Tetrahydroisoquinoline-1- carbonitriles can serve as starting materials for the one-pot synthesis of 5,6-dihydropyrrolo[2,1a]isoquinolines and 1-benzyl-3,4-dihydroisoquinolines. The latter compounds were transformed to lamellarin G trimethyl ether and lamellarin U in short reaction sequences. This method allows the introduction of acid-sensitive protecting groups for the phenolic hydroxy functions which would be cleaved under the harsh conditions of the classical Bischler-Napieralski reaction.

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.

Gaining diversity in solid-phase synthesis by modulation of cleavage conditions from hydroxymethyl-based supports. Application to lamellarin synthesis

The application of a number of Lewis acids as a cleavage/deprotection method in the solid-phase synthesis of organic molecules can render several analogues, which, after purification, can be submitted for biological evaluation.