Reddy, P Anantha and Rao, GS Krishna (1979) Studies in terpenoids. Part 42. Synthesis of 3-(2-hydroxyisopropyl)5,8-dimethyl-1,2-naphthoquinone (emmotin-H). In: Journal of Chemical Society, Perkin Transactions- 1, 1 . pp. 237-238.
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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).
|Item Type:||Journal Article|
|Additional Information:||Copyright of this article belongs to RSC Publishing.|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||04 Nov 2009 09:52|
|Last Modified:||19 Sep 2010 05:31|
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