New synthesis of Orelline by metalation of methoxypyridines

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Abstract

A new total synthesis in five steps of the alkaloid Orelline is reported. The methodology involves metalation of methoxypyridines to afford 2-halo-3,4-dimethoxypyridine on which an homocoupling reaction is performed to build the 2,2′-bipyridyl structure of the alkaloid. © 1993.

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Trécourt, F., Mallet, M., Mongin, O., Gervais, B., & Quéguiner, G. (1993). New synthesis of Orelline by metalation of methoxypyridines. Tetrahedron, 49(37), 8373–8380. https://doi.org/10.1016/S0040-4020(01)81920-7

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