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Terpenoids. LXXII. Iodoxybenzene oxidation of 1-naphthols: synthesis of mansonone A

Murali, D and Rao, Krishna GS (1987) Terpenoids. LXXII. Iodoxybenzene oxidation of 1-naphthols: synthesis of mansonone A. In: Indian Journal of Chemistry, Sect. B: Organic Chemistry including Medicinal Chemistry, 26 (7). pp. 668-670.

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Abstract

Substituted 1-naphthols I $(R_1-R_4=H$; $R_1=Me, R_2-R_4=H$; $R_1=R_2=R_4=H, R_3=Me, OMe$; $R_1-R_3=H, R_4=OMe$; $R_1=R_3=R_4=H, R_2=OMe$; etc.) were oxidized by $PhIO_2$ to afford a mixture of 1,2- and 1,4-naphthoquinones II and III. Similar oxidation of a tetrahydro-8-naphthol IV gives mansonone A (V) and a 1,4-quinone (VI). During oxidation $PhIO_2$ preserves intact labile structural features such as a benzylic tertiary hydroxyl group or a hydroarom. ring.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Council of Scientific & Industrial Research
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 18 Apr 2008
Last Modified: 27 Aug 2008 13:20
URI: http://eprints.iisc.ernet.in/id/eprint/13764

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