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2005
Indole derivatives
R 0140
Radical Cyclization Approach to Spirocyclohexadienones. — A new procedure for
synthesis of spirooxindoles and spirodihydroquinolones through ipso cyclization of
20- 112 the
aryl radicals to oxygen-substituted aromatic rings is described. The usefulness is shown
by the synthesis of a number of spirocyclic compounds, including key intermediates
(VIII) and (XIII) in the synthesis of SR121463A and aza-galanthamine. Substituents
favoring β-fragmentation (trityl) give more ipso-substitution product, while substituents disfavoring it (methyl) give more ortho-substitution product. —
(GONZALEZ-LOPEZ DE TURISO, F.; CURRAN*, D. P.; Org. Lett. 7 (2005) 1,
151-154; Dep. Chem., Univ. Pittsburgh, Pittsburgh, PA 15260, USA; Eng.) —
Steudel
2005
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