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

The Diels-Alder adducts of ethyl ( )-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...

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Bibliographic Details
Published in:Pure and applied chemistry 2009-01, Vol.81 (1), p.105-112
Main Authors: Bwire, Regina N., Majinda, Runner R., Masesane, Ishmael B., Steel, Patrick G.
Format: Article
Language:English
Subjects:
Adducts
Agrochemicals
Chemical reactions
Chemical synthesis
Derivatives
Diels-Alder reaction
Enantiomers
epoxidation
Natural products
nitroacrylate
Organic acids
Organic chemistry
oryzoxymycin
Oxidation
transfer hydrogenation
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Summary:The Diels-Alder adducts of ethyl ( )-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.
ISSN:0033-4545
1365-3075
DOI:10.1351/PAC-CON-07-12-04