From nature, through chemical synthesis, toward use in agriculture: Oryzoxymycin case study
Bwire, R N
Majinda, R R
Masesane, I B
Steel, P G
PublisherInternational Union of Pure and Applied Chemistry. http://stage.iupac.org/publications/pac/
MetadataShow full item record
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.