Tetrahedron letters

One-step synthesis of 2, 9-disubstituted phenanthrenes via Diels–Alder reactions using 1, 4-disubstituted naphthalenes as dienophiles

E Paredes, B Biolatto, M Kneeteman, P Mancini

Index: Paredes, Elisa; Biolatto, Betina; Kneeteman, Maria; Mancini, Pedro Tetrahedron Letters, 2002 , vol. 43, # 26 p. 4601 - 4603

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Citation Number: 24

Abstract

The normal electron-demand Diels–Alder reaction between 1, 4-disubstituted naphthalenes, nitro being one of these two groups, and 1-methoxy-3-trimethylsililoxy-1, 3-butadiene gives hydroxyphenanthrene derivatives, the yields being enhanced by placement of more electron- withdrawing groups on the dienophilic system. The nitro group as substituent directs the cycloaddition, and its cis-extrusion as nitrous acid along with the loss of methanol from ...