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Synthesis of Isoquinoline Alkaloid, (š)-Salsolidine, Using Thiazolino[2,3-a]isoquinolinone S-Oxide as Intermediate

Rozwadowska M. D., Sulima A.

Polish Journal of Chemistry

2001

Vol. 75, nr 12

1847-1852

Thiazolino[2,3-a]isoquinolinones have been oxidized to the corresponding S-oxides and their 10b-methyl derivatives desulfurized with Raney nickel to give (š) N-acyl salsolidine. Base-catalyzed hydrolysis of the N-acetyl derivative afforded (š)-salsolidine. C-Methylation reactions of the title heterocyclic system have been investigated throughly. Stereochemistry ofthe synthesized compounds nas been established.