Synthesis of 2-Alkyl-1,4-naphthoquinones via anortho-Directive Metalation

Abstract
Plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) has been shown to have a potent insect ecdysis inhibitory activity. To test the activity of synthetic analogs, the synthesis of 2-alkyl-1,4-naphthoquinones via an ortho-directive metalation using naphthol methoxymethyl ether as a directive group was carried out. This method is also applicable to the synthesis of naphthoquinones having unsaturated side-chain.

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