Journal of Organic Chemistry 2003-12-26

An efficient two-step total synthesis of the quaterpyridine nemertelline.

Alexandre Bouillon, Anne Sophie Voisin, Audrey Robic, Jean-Charles Lancelot, Valérie Collot, Sylvain Rault

Index: J. Org. Chem. 68(26) , 10178-80, (2003)

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Abstract

Regioselective and univocal Suzuki cross-coupling reactions performed on halopyridinyl boronic acids provide a flexible and versatile route to a multigram scale synthesis of 2,2'-dichloro-3,4'-bipyridine 14, which allows couplings with excess pyridin-3-yl boronic acid to give a new and efficient two-step rapid synthesis of nemertelline, the quaterpyridine neurotoxin isolated from a Hoplonemertine sea worm.