149378-56-3

Upstream product

• 121-33-5 vanillin 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 200941-16-8 2-[(4-Isopropoxy-3-methoxy-phenyl)ethynyl]-5-isopropoxy-4-methoxybenzaldehyde 
• 200941-18-0 5-Isopropoxy-2-(4-isopropoxy-3-methoxy-phenylethynyl)-4-methoxy-phenol 
• 200941-14-6 β,β-dibromo-4-isopropoxy-3-methoxystyrene 
• 2538-98-9 4-isopropyloxy-3-methoxybenzaldehyde 
• 621-59-0 isovanillin 
• 363134-22-9 5-isopropoxy-4-methoxy-2-trimethylsilanylethynyl-phenol 
• 363134-18-3 5-isopropoxy-4-methoxy-2-trimethylsilanylethynyl-benzaldehyde 
• 363134-23-0 1-ethynyl-2,4-diisopropoxy-5-methoxy-benzene 
• 200941-15-7 2-iodo-5-isopropoxy-4-methoxybenzaldehyde 
• 34123-66-5 O-isopropylisovanillin 
• 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 
• 2103-57-3 2,3,4-trimethoxybenzaldehyde 

Downstream Products

• 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 
• 149378-58-5 lamellarin M 
• 149355-78-2 14-(4-acetoxy-3-methoxyphenyl)-3,10-diacetoxy-2,11,12-trimethoxy-8,9-dihydro-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.

Biomimetic syntheses of lamellarin and lukianol-type alkaloids

The formation of 3,4-diarylpyrrole-2,5-dicarboxylic acids from arylpyruvic acids and 2-arylethylamines was used as a key step for the synthesis of several marine pyrrole alkaloids. The utility of this method is illustrated through the development of synth

A highly efficient synthesis of lamellarins K and L by the Michael addition/ring-closure reaction of benzyldihydroisoquinoline derivatives with ethoxycarbonyl-β-nitrostyrenes

Alkaloid achievement: Lamellarins, a new class of potential nontoxic inhibitors of HIV-1 integrase that are also responsible for multidrug-resistance reversal in cancer cell lines, could be synthesized in three chemical steps and in 60% overall yields fro

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

Syntheses of lamellarins I and K by [3+2] cycloaddition of a nitrone to an alkyne

Lamellarins I and K were obtained by a new approach based on the 1,3-dipolar cycloaddition of a nitrone to an alkyne. The key cycloaddition yields an isoxazoline which rearranges to afford the central pyrrole ring.

Convergent total synthesis of lamellarin K

The azomethine ylide derived from dihydroisoquinolinium salt 24 undergoes an intramolecular [3 + 2] cycloaddition reaction to give pyrrole 25 which upon de-isopropylation affords the marine alkaloid lamellarin K 4.