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

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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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).

Item Type:	Journal Article
Publication:	Journal of Chemical Society, Perkin Transactions- 1
Publisher:	RSC Publishing
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
URI:	http://eprints.iisc.ac.in/id/eprint/20176

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