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Synthesis 1986; 1986(5): 431-433
DOI: 10.1055/s-1986-31669
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Synthesis of 2-Alkyl-1,4-naphthoquinones via an ortho-Directive Metalation

Tadao Kamikawa* , Isao Kubo
  • *Department of Chemistry, Faculty of Science & Technology, Kinki University, Kowakae, Higashi-Osaka 577, Japan
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Publication Date:
27 September 2002 (online)

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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.