e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

A regiospecific synthesis of protoberberine alkaloids

…, J Poplawski, BC Nalliah, DB MacLean

Index: Kiparissides, Zinovia; Fichtner, Robert H.; Poplawski, Janusz; Nalliah, Bala C.; MacLean, David B. Canadian Journal of Chemistry, 1980 , vol. 58, p. 2770 - 2779

Full Text: HTML

Citation Number: 31

Abstract

The protoberberine skeleton has been prepared in two steps from N-benzyl-3, 4- dihydroisoquinolinium salts. Treatment of the salts with the anion of methyl methylthiomethylsulfoxide yields mixtures of diastereomeric adducts that cyclize on heating with concentrated hydrochloric acid to dihydroprotoberberines. The latter compounds may be reduced to their tetrahydro analogues with sodium borohydride, oxidized to ...

Benzo[d][1,3]dioxol-4-ylmethanol Structure

Benzo[d][1,3]di...

~67%

4-(chloromethyl)benzo[d][1,3]dioxole Structure

4-(chloromethyl...

Tetrahydropalmatine Structure

Tetrahydropalmatine

~92%

2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

6,7-Dimethoxyisoquinoline Structure

6,7-Dimethoxyis...

~%

2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

Dehydroheliamine Structure

Dehydroheliamine

~%

2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

2-(2,3-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium bromide Structure

2-(2,3-dimethox...

~%

2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

2-(2,3-dimethoxybenzyl)-6,7-dimethoxy-1-((methylsulfinyl)(methylthio)methyl)-1,2-dihydroisoquinoline Structure

2-(2,3-dimethox...

~%

2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

2-(2,3-dimethoxybenzyl)-6,7-dimethoxy-1-((methylsulfinyl)(methylthio)methyl)-1,2,3,4-tetrahydroisoquinoline Structure

2-(2,3-dimethox...

~%

2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

6,7-dimethoxy-N-(2,3-dimethoxybenzyl)isoquinolinium chloride Structure

6,7-dimethoxy-N...

~%

2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

2,3-dimethoxybenzyl chloride Structure

2,3-dimethoxybe...

~%

2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

2,3-Dimethoxybenzylbromide Structure

2,3-Dimethoxybe...

~%

2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

dihydropalmatine Structure

dihydropalmatine

~%

2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

dihydropalmatine chloride Structure

dihydropalmatin...

~%

2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

dihydropalmatine Structure

dihydropalmatine

~75%

Tetrahydropalmatine Structure

Tetrahydropalmatine

dihydropalmatine chloride Structure

dihydropalmatin...

~90%

Tetrahydropalmatine Structure

Tetrahydropalmatine

6,7-Dimethoxyisoquinoline Structure

6,7-Dimethoxyis...

~%

Tetrahydropalmatine Structure

Tetrahydropalmatine

Dehydroheliamine Structure

Dehydroheliamine

~%

Tetrahydropalmatine Structure

Tetrahydropalmatine

2-(2,3-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium bromide Structure

2-(2,3-dimethox...

~%

Tetrahydropalmatine Structure

Tetrahydropalmatine

2-(2,3-dimethoxybenzyl)-6,7-dimethoxy-1-((methylsulfinyl)(methylthio)methyl)-1,2-dihydroisoquinoline Structure

2-(2,3-dimethox...

~%

Tetrahydropalmatine Structure

Tetrahydropalmatine

2-(2,3-dimethoxybenzyl)-6,7-dimethoxy-1-((methylsulfinyl)(methylthio)methyl)-1,2,3,4-tetrahydroisoquinoline Structure

2-(2,3-dimethox...

~%

Tetrahydropalmatine Structure

Tetrahydropalmatine

6,7-dimethoxy-N-(2,3-dimethoxybenzyl)isoquinolinium chloride Structure

6,7-dimethoxy-N...

~%

Tetrahydropalmatine Structure

Tetrahydropalmatine

2,3-dimethoxybenzyl chloride Structure

2,3-dimethoxybe...

~%

Tetrahydropalmatine Structure

Tetrahydropalmatine

Formaldehyde Structure

dihydropalmatine chloride Structure

dihydropalmatin...

~65%

2,3,9,10-tetramethoxy-13-methyl-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

6,7-Dimethoxyisoquinoline Structure

6,7-Dimethoxyis...

~%

2,3,9,10-tetramethoxy-13-methyl-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

2-(2,3-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium bromide Structure

2-(2,3-dimethox...

~%

2,3,9,10-tetramethoxy-13-methyl-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

2-(2,3-dimethoxybenzyl)-6,7-dimethoxy-1-((methylsulfinyl)(methylthio)methyl)-1,2-dihydroisoquinoline Structure

2-(2,3-dimethox...

~%

2,3,9,10-tetramethoxy-13-methyl-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

6,7-dimethoxy-N-(2,3-dimethoxybenzyl)isoquinolinium chloride Structure

6,7-dimethoxy-N...

~%

2,3,9,10-tetramethoxy-13-methyl-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

2,3-dimethoxybenzyl chloride Structure

2,3-dimethoxybe...

~%

2,3,9,10-tetramethoxy-13-methyl-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

2,3-Dimethoxybenzylbromide Structure

2,3-Dimethoxybe...

~%

2,3,9,10-tetramethoxy-13-methyl-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

2-(2,3-dimethoxybenzyl)-6,7-dimethoxy-1-((methylsulfinyl)(methylthio)methyl)-1,2,3,4-tetrahydroisoquinoline Structure

2-(2,3-dimethox...

~%

2,3,9,10-tetramethoxy-13-methyl-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...

Dehydroheliamine Structure

Dehydroheliamine

~%

2,3,9,10-tetramethoxy-13-methyl-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium,iodide Structure

2,3,9,10-tetram...