Synthesis of (-)-cytoxazone and (+)-epi-cytoxazone: The chiral pool approach
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Immunomodulator (-)-cytoxazone and its epimer (+)-epi-cytoxazone were synthesized starting from (D)-(-)-4-hydroxyphenylglycine. Homologation of the amino acid was achieved via the corresponding aldehyde, by a cyanohydrin reaction. The racemization of highly sensible amido aldehyde was efficiently suppressed when the oxidation of the parent aminoalcohol was performed by a modified Dess-Martin procedure.
Keywords:amino alcohols / cyanohydrins / cytoxazone / oxazolines
Source:Synthetic Communications, 2005, 35, 3, 435-447
- Marcel Dekker Inc, New York