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Paper | Regular issue | Vol 100, No. 2, 2020, pp.225-240
Published online, 14th February, 2020
DOI: 10.3987/COM-20-14219
Concise Synthesis and Evaluation of ortho-Naphthoquinones Containing a Phenolic Hydroxy Moiety

Mitsuaki Yamashita, Syuhei Hata, Jun Sawano, Ryuji Umeda, and Akira Iida*

*School of Agriculture, Kindai University, Nakamachi, Nara 631-8505, Japan

Abstract

A concise and efficient synthesis method for the preparation of antiproliferative ortho-naphthoquinones is described. Notably, the synthesis of ortho-furanonaphthoquinone was achieved by utilizing a regioselective oxidative conjugate addition of dimethylamine and the Sonogashira coupling/cyclization reaction as the key steps. Additionally, an improved synthesis of hydroxy-β-lapachone was established and included a regioselective prenylation by directed ortho-lithiation. In vitro antiproliferative effects of the synthesized analogs against a panel of 39 human cancer cell lines were evaluated and the results were directly compared to those previously obtained for 1.