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

Full Text: HTML

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 ...

Related Articles:

Synthesis and cytotoxicity on human leukemia cells of furonaphthoquinones isolated from tabebuia plants

[Inagaki, Ryuta; Ninomiya, Masayuki; Tanaka, Kaori; Watanabe, Kunitomo; Koketsu, Mamoru Chemical and Pharmaceutical Bulletin, 2013 , vol. 61, # 6 p. 670 - 673]

A facile synthesis of naturally occurring binaphthoquinones: efficient oxidative dimerization of 4-alkoxy-1-naphthols using silver (II) oxide–40% nitric acid

[Tanoue, Yasuhiro; Sakata, Kazunori; Hashimoto, Mamoru; Morishita, Shin-Ich; Hamada, Moritsugu; Kai, Norihisa; Nagai, Takeshi Tetrahedron, 2002 , vol. 58, # 1 p. 99 - 104]

The synthesis of 6-deoxyanthracyclinones:(±) α-citromycinone and (±) 4-demethoxy-6-deoxydaunomycinone

[Swenton, John S.; Anderson, D. Keith; Coburn, Charles E.; Haag, Anthony P. Tetrahedron, 1984 , vol. 40, # 22 p. 4633 - 4642]

Oxidative degradation approach to p-quinones

[Saa, Jose M.; Morey, Jeronimo; Rubido, Carmen Journal of Organic Chemistry, 1986 , vol. 51, # 23 p. 4471 - 4473]

1, 4-Dimethoxy-1, 3-butadiene as a donor diene in Diels-Alder cycloadditions

[Hiranuma Hidetoshi; Miller, Sidney I. Journal of Organic Chemistry, 1982 , vol. 47, # 26 p. 5083 - 5088]

More Articles...