Synthesis of cicerfuran, an antifungal benzofuran, and some related analogues |
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Authors: | Shazia N. Aslam Sara J. Phythian David R. Hall |
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Affiliation: | a Natural Resources Institute, University of Greenwich, Chatham Maritime, Kent ME4 4TB, UK b Jodrell Laboratory, Royal Botanic Gardens, Kew, Richmond, Surrey TW9 3DS, UK |
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Abstract: | Routes were investigated for the synthesis of cicerfuran, a hydroxylated benzofuran from wild chickpea implicated in resistance to Fusarium wilt, and some of its analogues. A novel method is described for the synthesis of oxygenated benzofurans by epoxidation and cyclisation of 2′-hydroxystilbenes. The stilbene intermediates required could be synthesised by palladium-catalysed coupling of styrenes with mono-oxygenated aryl halides but not with di-oxygenated aryl halides. Stilbenes corresponding to the latter were synthesised by Wittig reactions. |
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Keywords: | Cicerfuran Arylbenzofuran Palladium-catalysed coupling Wittig reaction |
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