Simple Synthesis of 2-Acetyl-5,8-dimethoxy-3,4-dihydronaphthalene: A Key Intermediate for the Synthesis of 4-Demethoxydaunomycinone
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Subhash P. Chavan, Y. Tripura Subbarao and Chittiboyina Amar Gopal
Abstract
2-Acetyl-5,8-dimethoxy-3,4-dihydronaphthalene is prepared by using a 1,3-dipolar cycloaddition of nitrile oxide to the corresponding dihydronaphthalene.
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