Bwire, R N; Majinda, R R; Masesane, I B; Steel, P G(International Union of Pure and Applied Chemistry. http://stage.iupac.org/publications/pac/, NaN, 2009)
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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.