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An efficient route to 3-chlorojuglones

✍ Scribed by James L. Bloomer; Joseph A. Gazzillo

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
208 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

The novel 4-chloro-2,5-dimethoxybenzaldehyde 1 has been prepared and converted in only three steps to 5-acetoxy-7-carboethoxy-3-chloro-l,4-naphthaquinone 4. Subsequent Diels-Alder reaction affords a tetracyclic enol ether 2 in a regiospecific manner. Failure of simple juglones to undergo regiospecific reaction in the Diels-Alder synthesis of anthracyclines and other natural products has led to the development of 3-halojuglones for that purpose'. The present communication describes the preparation of the novel chloroaldehyde 1 and its conversion in only three steps to the chlorojuglone derivative 4.

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