Anodic Addition Reactions of 1, 5-Dimethoxy- and 1,4,5-Trimethoxynaphthalenes. A Convenient Synthesis of Methoxyjuglone
Authors:
- 1 January 1977
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 7 (5) , 333-337
Abstract
While anodic oxidation of substituted benzenes and anthracenes has been extensively studied, there are few studies of naphthalene derivatives.1 Our need for a convenient economical route to methoxyjuglone2 prompted an investigation of the anodic oxidation of 1, 5-dimethoxynaphthalene, 1. 3,4 We report that preparative anodic oxidation of 1 affords an isolable 1, 4-dihydronaphthalene, 2, which is converted to 1, 4, 5-trimethoxynaphthalene, 3, by acid. Subsequent anodic oxidation of 3 followed by acid hydrolysis affords methoxyjuglone, a versatile intermediate in anthracycline synthesis.Keywords
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