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À propos de : Syntheses of (−)-Funebrine and (−)-Funebral, Using SequentialTransesterification and Intramolecular Cycloaddition of a ChiralNitrone        

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  • Syntheses of (−)-Funebrine and (−)-Funebral, Using SequentialTransesterification and Intramolecular Cycloaddition of a ChiralNitrone
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  • The first syntheses of (−)-funebrine [(−)-1] and (−)-funebral [(−)-2] are described. The synthesesfeature 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 resultingnitrone VII bearing crotyl ester to afford cycloadduct 7 as a major product. The adduct 7 was readilyelaborated to amino lactone (−)-3, the key synthetic intermediate of (−)-1 and (−)-2.
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