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

Bwire, Regina N.; Majinda, Runner R.; Masesane, Ishmael B.; Steel, Patrick G.

doi:10.1351/PAC-CON-07-12-04

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

http://dx.doi.org/10.1351/PAC-CON-07-12-04

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.