Synthesis of (-)-cytoxazone and (+)-epi-cytoxazone: The chiral pool approach
Апстракт
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.
Кључне речи:
amino alcohols / cyanohydrins / cytoxazone / oxazolinesИзвор:
Synthetic Communications, 2005, 35, 3, 435-447Издавач:
- Marcel Dekker Inc, New York
DOI: 10.1081/SCC-200048953
ISSN: 0039-7911
WoS: 000227372500012
Scopus: 2-s2.0-14644411112
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Tokic-Vujosevic, Z AU - Petrović, G. AU - Rakic, B AU - Matović, Radomir AU - Saičić, Radomir PY - 2005 UR - https://cherry.chem.bg.ac.rs/handle/123456789/688 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 - Marcel Dekker Inc, New York 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 Rakic, B and Matović, Radomir and Saičić, Radomir", 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 = "Marcel Dekker Inc, New York", 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., Rakic, B., Matović, R.,& Saičić, R.. (2005). Synthesis of (-)-cytoxazone and (+)-epi-cytoxazone: The chiral pool approach. in Synthetic Communications Marcel Dekker Inc, New York., 35(3), 435-447. https://doi.org/10.1081/SCC-200048953
Tokic-Vujosevic Z, Petrović G, Rakic B, Matović R, Saičić R. 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., Rakic, B, Matović, Radomir, Saičić, Radomir, "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 . .