Issue 0, 1979
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Studies in terpenoids. Part 42. Synthesis of 3-(2-hydroxyisopropyl)5,8-dimethyl-1,2-naphthoquinone (emmotin-H)

P. Anantha Reddy  and  G. S. Krishna Rao  

Abstract

Emmotin-H, a naturally occurring sesquiterpenoid 1,2-naphthoquinone pigment (1) has been synthesised in a four step sequence starting from the known 5,8-dimethyl-4-oxotetralin-2-carboxylic acid (3a). Selenium dioxide oxidation of its methyl ester (3b) gives 3-methoxycarbonyl-5,8-dimethyl-1,2-naphthoquinone (4) which on reductive acetylation affords the corresponding diacetoxynaphthalene ester (5). Its reaction with excess of methylmagnesium iodide is accompanied by aerial oxidation during work-up and furnishes emmotin-H (1).

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Article information

DOI
https://doi.org/10.1039/P19790000237
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1979, 237-238

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Studies in terpenoids. Part 42. Synthesis of 3-(2-hydroxyisopropyl)5,8-dimethyl-1,2-naphthoquinone (emmotin-H)

P. A. Reddy and G. S. K. Rao, J. Chem. Soc., Perkin Trans. 1, 1979, 237 DOI: 10.1039/P19790000237

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