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Pure Appl. Chem., 2009, Vol. 81, No. 1, pp. 105-112

From nature, through chemical synthesis, toward use in agriculture: Oryzoxymycin case study

Regina N. Bwire1, Runner R. Majinda1, Ishmael B. Masesane1 and Patrick G. Steel2

1 Department of Chemistry, University of Botswana, P/Bag 00704, Gaborone, Botswana
2 Department of Chemistry, University of Durham, South Road, Durham DH1 3LE, UK

Abstract: The Diels-Alder adducts of ethyl (E)-3-nitroacrylate and furan provided a common and versatile template for the stereocontrolled synthesis of an isomer of the natural product oryzoxymycin and polyhydroxylated cyclohexyl β-amino acid derivatives. The strategy for the synthesis of the polyhydroxylated cyclic β-amino acid derivatives involved base-induced fragmentation of the oxanorbornene skeleton and face selective oxidation reactions. A Pd-catalyzed transfer hydrogenation reaction in the presence of organic acids is also described. This reaction is amenable to being enantioselective through use of optical pure chiral organic acids.