An efficient two-step total synthesis of the quaterpyridine nemertelline.
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.
Bouillon
Alexandre
A
Centre d'Etudes et de Recherche sur le Médicament de Normandie, UFR des Sciences Pharmaceutiques, 5 rue Vaubénard, 14032 Caen, France.
Voisin
Anne Sophie
AS
Robic
Audrey
A
Lancelot
Jean-Charles
JC
Collot
Valérie
V
Rault
Sylvain
S
D001897:Boronic Acids / Q000737:chemistry; D015394:Molecular Structure; D009498:Neurotoxins / Q000138:chemical synthesis*; D011725:Pyridines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001897:Boronic Acids; D009498:Neurotoxins; D011725:Pyridines; C482881:nemertelline