Tetrahedron

Pyridine radicals in synthesis. Part 3: Cyclopentannulation of pyridine via the 3-pyridyl radical and a formal synthesis of (±)-Oxerine

K Jones, A Fiumana, ML Escudero-Hernandez

文献索引：Jones, Keith; Fiumana, Andrea; Escudero-Hernandez, Maria L. Tetrahedron, 2000 , vol. 56, # 3 p. 397 - 406

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被引用次数: 28

摘要

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.