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  • Title: Total syntheses of (-)-fructigenine A and (-)-5-N-acetylardeemin.
    Author: Takiguchi S, Iizuka T, Kumakura YS, Murasaki K, Ban N, Higuchi K, Kawasaki T.
    Journal: J Org Chem; 2010 Feb 19; 75(4):1126-31. PubMed ID: 20073509.
    Abstract:
    The first total synthesis of (-)-fructigenine A and a novel approach to (-)-5-N-acetylardeemin through a common imine intermediate (+)-3 are described. The key steps include highly enantioselective preparation of (+)-3 via domino olefination/isomerization/Claisen rearrangement (OIC) of 5, reductive cyclization (RC), and regioselective oxidation of (-)-4 and a novel assembly of the pyrazino ring of these alkaloids via Ugi three-component reaction/cyclization of (+)-3 with the corresponding amino acid and isonitrile.
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