Pyridine radicals in synthesis. Part 3: Cyclopentannulation of pyridine via the 3-pyridyl radical and a formal synthesis of (±)-oxerine
The allylation and propargylation of 3-bromo-4-formylpyridine under zinc-mediated Barbier conditions is described. The homoallylic alcohols produced are cyclised via the derived 3-pyridyl radical to give cyclopentannulated pyridines. One of these bicyclic compounds is converted into an advanced intermediate in a previous synthesis of the monoterpene alkaloid (±)-oxerine. (C) 2000 Elsevier Science Ltd.
Jones, Keith,Fiumana, Andrea,Escudero-Hernandez, Maria L.
p. 397 - 406
(2007/10/03)
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