Synthesis of (-)-cytoxazone and (+)-epi-cytoxazone: The chiral pool approach

Abstract

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.