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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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 |
|---|---|
| Publication: | Indian Journal of Chemistry, Sect. B: Organic Chemistry including Medicinal Chemistry |
| Publisher: | Council of Scientific & Industrial Research |
| 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.ac.in/id/eprint/13764 |
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