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Synthesis of cicerfuran, an antifungal benzofuran, and some related analogues

Synthesis of cicerfuran, an antifungal benzofuran, and some related analogues

Aslam, Shazia N., Stevenson, Philip C. ORCID: 0000-0002-0736-3619, Phythian, Sara J., Veitch, Nigel C. and Hall, David R. ORCID: 0000-0002-7887-466X (2006) Synthesis of cicerfuran, an antifungal benzofuran, and some related analogues. Tetrahedron, 62 (17). pp. 4214-4226. ISSN 0040-4020 (doi:10.1016/j.tet.2006.02.015)

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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 20-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

Item Type: Article
Uncontrolled Keywords: Cicerfuran, Arylbenzofuran, palladium-catalysed coupling, Wittig reaction
Subjects: S Agriculture > S Agriculture (General)
Q Science > Q Science (General)
Q Science > QD Chemistry
S Agriculture > SB Plant culture
Faculty / Department / Research Group: Faculty of Engineering & Science > Natural Resources Institute
Faculty of Engineering & Science > Natural Resources Institute > Agriculture, Health & Environment Department
Related URLs:
Last Modified: 11 Nov 2011 12:06
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
URI: http://gala.gre.ac.uk/id/eprint/3158

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