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.
TY - JOUR
AU - Tokic-Vujosevic, Z
AU - Petrović, G
AU - Rakić, B
AU - Matović, Radomir
AU - Saičić, Radomir N.
PY - 2005
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2769
AB - 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.
PB - Taylor & Francis
T2 - Synthetic Communications
T1 - Synthesis of (-)-cytoxazone and (+)-epi-cytoxazone: The chiral pool approach
VL - 35
IS - 3
SP - 435
EP - 447
DO - 10.1081/SCC-200048953
ER -
@article{
author = "Tokic-Vujosevic, Z and Petrović, G and Rakić, B and Matović, Radomir and Saičić, Radomir N.",
year = "2005",
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.",
publisher = "Taylor & Francis",
journal = "Synthetic Communications",
title = "Synthesis of (-)-cytoxazone and (+)-epi-cytoxazone: The chiral pool approach",
volume = "35",
number = "3",
pages = "435-447",
doi = "10.1081/SCC-200048953"
}
Tokic-Vujosevic, Z., Petrović, G., Rakić, B., Matović, R.,& Saičić, R. N.. (2005). Synthesis of (-)-cytoxazone and (+)-epi-cytoxazone: The chiral pool approach. in Synthetic Communications
Taylor & Francis., 35(3), 435-447.
https://doi.org/10.1081/SCC-200048953
Tokic-Vujosevic Z, Petrović G, Rakić B, Matović R, Saičić RN. Synthesis of (-)-cytoxazone and (+)-epi-cytoxazone: The chiral pool approach. in Synthetic Communications. 2005;35(3):435-447.
doi:10.1081/SCC-200048953 .
Tokic-Vujosevic, Z, Petrović, G, Rakić, B, Matović, Radomir, Saičić, Radomir N., "Synthesis of (-)-cytoxazone and (+)-epi-cytoxazone: The chiral pool approach" in Synthetic Communications, 35, no. 3 (2005):435-447,
https://doi.org/10.1081/SCC-200048953 . .
, 
