144709-27-3

Upstream product

• 108-24-7 acetic anhydride 
• 38846-64-9 2-ethynylbenzaldehyde 
• 35345-49-4 2-iodo-4,5-dimethoxyphenylacetic acid methyl ester 
• 67-56-1 methanol 
• 144709-15-9 [4,5-Dimethoxy-2-(1-oxo-1,2-dihydro-isoquinolin-3-yl)-phenyl]-acetic acid 

Downstream Products

• 144709-16-0 3<2-hydroxyethyl-4,5-dimethoxyphenyl>-1(2H)-isoquinolone 
• 144709-19-3 N-methyl-3-<2-hydroxyethyl-4,5-dimethoxyphenyl>-1(2H)-isoquinolone 
• 144709-18-2 N-methyl-3-<2-(methoxycarbonylmethyl)-4,5-dimethoxyphenyl>-1(2H)-isoquinolone 

Relevant academic research and scientific papers

Total Synthesis of Two 8-Oxoprotoberberine Alkaloids: Alangiumkaloids A and B

A new and versatile synthetic route for 8-oxoprotoberberine 17 through synthesis of isoquinolinone 16 and construction of a B-ring is described. The key step is the synthesis of isoquinolinone 14 through thermal cyclization of 2-alkynylbenzaldehyde oxime 12 to afford isoquinoline N-oxide 13, followed by a Reissert–Henze-type reaction. The first total synthesis of 8-oxoprotoberberine alkaloid alangiumkaloids A and B was achieved by using this strategy.

A common and general access to berberine and benzo [c] phenanthridine alkaloids

The S(RN)1 reactions between o-iodobenzamides and the enolate anion from 2-acetyl homoveratric acid lead to key tricyclic compounds which are easily converted to either berberine or benzo [c] phenanthridine ring systems providing thus a highly-yielding and versatile access to both classes of alkaloids.