871731-74-7

Upstream product

• 93189-18-5 N-(7-methoxynaphthalen-1-yl)acetamide 
• 108-24-7 acetic anhydride 
• 118-46-7 8-amino-2-naphthol 
• 5302-79-4 7-methoxynaphthalen-1-amine 

Downstream Products

• 871731-76-9 N-acetyl-(3-acetyl-7-methoxy-1-naphthalenyl)carbamic acid 1,1-dimethylethyl ester 
• 871731-93-0 N-(7-hydroxy-3-methyl-1-naphthalenyl)-3-methoxybenzamide 
• 871731-95-2 2-(3-methoxyphenyl)-7-methylbenz[cd]indol-3(1H)-one 
• 871731-94-1 N-{4,8-dibromo-3-methyl-7-[[tris(1-methylethyl)silyl]oxy]-1-naphthalenyl}-3-methoxybenzamide 

Relevant academic research and scientific papers

Synthesis of HKI 0231B

The total synthesis of HKI 0231B (1b) was completed in 12 linear steps and 15.6% overall yield. An unusual anionic cyclization provided access to intermediate 61 and the embedded benz[cd]-indol-3-(1H)-one ring system 3. Directed ortho-lithiation in the presence of a ketone followed by formylation and finally acid-catalyzed methanolysis complete the synthesis. Studies directed toward the construction and reactivity of the lactam acetal functionality present in HKI 0231A (1a) are also reported.