149355-78-2

Upstream product

• 75-36-5 acetyl chloride 
• 149378-56-3 lamellarin K 
• 47811-28-9 5-Benzyloxy-1-(4-benzyloxy-3-methoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 121-33-5 vanillin 
• 680189-47-3 ethyl 1-(4-benzyloxy-3-methoxyphenyl)-2-(2,4-dibenzyloxy-5-methoxyphenyl)-7-benzyloxy-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate 
• 680189-49-5 2-(2,4-dihydroxy-5-methoxy-phenyl)-7-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)-8,9-dimethoxy-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-3-carboxylic acid ethyl ester 
• 2103-57-3 2,3,4-trimethoxybenzaldehyde 
• 1034028-91-5 (Z)-ethyl 2,4-bis(benzyloxy)-5-methoxy-α-nitrocinnamate 
• 15778-62-8 2-(2-benzyloxy-3,4-dimethoxyphenyl)ethylamine 
• 35178-88-2 N-[2-(2-Benzyloxy-3,4-dimethoxy-phenyl)-ethyl]-2-(4-benzyloxy-3-methoxy-phenyl)-acetamide 
• 15778-61-7 2-Benzyloxy-3,4-dimethoxy-β-nitrostyren 
• 6527-13-5 3,4-dimethoxy-(phenylmethoxy)benzaldehyde 
• 19283-70-6 3,4-dimethoxysalicylaldehyde 

Downstream Products

• 149378-58-5 lamellarin M 
• 187156-56-5 14-(4-acetoxy-3-methoxyphenyl)-3,10-diacetoxy-2,11,12-trimethoxy-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 

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.

ANTITUMORAL ANALOGS OF LAMELLARINS

New lamellarins are provided of the general formula III wherein X is selected from the group consisting of N, O and S; wherein R1, R2, R3, R4, R5, R6, R7, R8 and Rsub