In the synthesis done by Tiecco, M. "et al." can be seen in the scheme below. In the first step, 3-hydroxy pyridine was first treated with bromine in an alkaline solution to obtain 2. The product of that step was then subjected to O-alkylation using DMF as a solvent to obtain 3. 3 was the oxidized with m-chloroperbenzoic acid in chloroform to give 4. That product was then nitrated with nitric acid and sulfuric acid to obtain a mixture of 5 and 6. These two molecules were separated by combining the mixture of products with water. 5 is insoluble in water, whereas 6 is soluble in water. 6 was then subjected to sodium methoxide in methanol to obtain the other methoxy group seen in product 7 and 7 was deoxygenated using phosphorus tribromide to obtain 8. To obtain tetramethyl orelline, structure 9, triphenylphosphine, NiCl2·6H2O, and zinc powder were used to conduct the homocoupling of halopyridines through the use of nickel-phosphine complexes. Once 8 with the bipyridyl structure had been obtained, the synthesis of orellanine could be conducted. The bipyridyl product from number 8 is then dealkylated with hydrobromic acid to give orelline, which was found to be a yellow crystalline solid (10). Orelline is then oxidized with hydrogen peroxide using heat to obtain the desired product, orellanine (11).