203787-18-2

Upstream product

• 203787-14-8 2-chloro-3-hydroxy-4-(trimethylsilyl)pyridine 
• 203787-13-7 2-chloro-3-(trimethylsilyloxy)pyridine 
• 89241-38-3 1,3-dimethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole 
• 203787-16-0 2-chloro-3-(trifluoromethanesulfonyloxy)-4-(trimethylsilyl)pyridine 
• 6636-78-8 2-chloro-3-hydroxypyridine 

Relevant academic research and scientific papers

Synthesis of ellipticine by hetaryne cycloadditions - Control of regioselectivity

We have modified Gribble's and Moody's approaches to ellipticines by introducing substituents into the 3,4-didehydropyridine dienophile to control the key cycloaddition step. A chloro substituent at position 2 improved the yields and the regioselectivities of the cycloadditions and the overall efficiency of the synthesis of ellipticine.

Polar Control of the Regioselectivity of Hetaryne Cycloadditions. Synthesis of Ellipticine

A regioselective cycloaddition between 1,3-dimethyl-4-(phenylsulfonyl)-4H-furoindole and 2-chloro-3,4-didehydropyridine is the key step of a modification of Gribble's approach to ellipticines.The use of a fluoride-promoted elimination for the generation of the pyridine and the control of the regioselectivity of the cycloaddition improve the yield of ellipticine by a factor of 3.