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Disubstituted Tetronic Natural Products

Lactonization of a hydroxy-acid to a butyrolactone is achieved, using dimethyl-formamide dineopentyl acetal, during a synthesis of oxygenated nor-heliango-lides. The chiral lactone (164) is prepared from (iJ)-malic acid, its dianion is alkylated at carbon to give the /ra/i5-disubstituted lactone (165) in moderate yield, and this is used in a synthesis of (—)-aplysistatin (Scheme 94). An independent, biogenetically patterned synthesis of this natural product, using tetronic acid intermediates, has been described. ... [Pg.135]

See other pages where Disubstituted Tetronic Natural Products is mentioned: [Pg.25]    [Pg.25]    [Pg.27]    [Pg.29]    [Pg.33]    [Pg.35]    [Pg.37]    [Pg.39]    [Pg.25]    [Pg.25]    [Pg.27]    [Pg.29]    [Pg.33]    [Pg.35]    [Pg.37]    [Pg.39]   


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