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  • Title: Syntheses of (-)-funebrine and (-)-funebral, using sequential transesterification and intramolecular cycloaddition of a chiral nitrone.
    Author: Tamura O, Iyama N, Ishibashi H.
    Journal: J Org Chem; 2004 Mar 05; 69(5):1475-80. PubMed ID: 14986999.
    Abstract:
    The first syntheses of (-)-funebrine [(-)-1] and (-)-funebral [(-)-2] are described. The syntheses feature sequential formation of nitrone VI from methyl glyoxylate (5) with oxime 6, transesterification of nitrone VI with (E)-crotyl alcohol (4), and intramolecular cycloaddition of the resulting nitrone VII bearing crotyl ester to afford cycloadduct 7 as a major product. The adduct 7 was readily elaborated to amino lactone (-)-3, the key synthetic intermediate of (-)-1 and (-)-2.
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