Synthesis of (−)-Cytoxazone and (+)-epi-Cytoxazone: The Chiral Pool Approach

Synthesis of (−)-Cytoxazone and (+)-epi-Cytoxazone: The Chiral Pool Approach

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 su...

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Bibliographic Details
Published in:Synthetic communications Vol. 35; no. 3; pp. 435 - 447
Main Authors: Tokic-Vujosevic, Zorana, Petrovic, Goran, Rakic, Bojana, Matovic, Radomir, Saicic, Radomir N.
Format: Journal Article
Language:English
Published: Taylor & Francis Group 01-01-2005
Subjects:
Amino alcohols
cyanohydrins
cytoxazone
oxazolines
Online Access:Get full text
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Summary: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.
ISSN:0039-7911
1532-2432
DOI:10.1081/SCC-200048953