Oxidation of 1, 5-naphthalenediol and its methyl ether: preparation of juglone methyl ether monoacetal

DJ Crouse, MM Wheeler, M Goemann…

Index: Crouse, David J.; Wheeler, Margaret M.; Goemann, Marti; Tobin, Paul S.; Basu, Swapan K.; Wheeler, Desmond M. S. Journal of Organic Chemistry, 1981 , vol. 46, # 9 p. 1814 - 1817

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Citation Number: 30

Abstract

Thallium trinitrate (TTN) oxidizes 1, 5-naphthalenediol (la) and its monomethyl ether (lb) in good yield to juglone (2a) and its methyl ether (2b), respectively. Oxidation of lb with TTN in a mixture of ethylene glycol and trimethyl orthoformate gave 2c (the 4-monoacetal of 2b), which is a promising intermediate in the synthesis of daunomycinone (3a) and some of its analogues. This is the first direct oxidation of a para-unsubstituted phenol to a monoacetal ...