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Stereoselective synthesis of (-)-cytoxazone and (+)-epi-cytoxazone

Authorized Users Only
2004
Authors
Milićević, Selena
Matović, Radomir
Saičić, Radomir N.
Article (Published version)
,
Elsevier
Metadata
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Abstract
Optically pure (-)-cytoxazone was synthesized, starting from methyl p-methoxycinnamate, in six steps and in 31%, overall yield. The required anti-aminoalcohol configuration was established by combining Sharpless asymmetric aminohydroxylation with the configurational inversion of the intermediate amidoalcohol via ail oxazoline. The synthesis of (+)-epi-cytoxazone is also described. (C) 2003 Elsevier Ltd. All rights reserved.
Keywords:
cytoxazone / asymmetric synthesis / natural products / immunosuppressive compounds / amino alcohols
Source:
Tetrahedron Letters, 2004, 45, 5, 955-957
Publisher:
  • Oxford : Pergamon-Elsevier Science Ltd

DOI: 10.1016/j.tetlet.2003.11.096

ISSN: 0040-4039

WoS: 000188380400015

Scopus: 2-s2.0-0346392218
[ Google Scholar ]
45
43
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/2762
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Milićević, Selena
AU  - Matović, Radomir
AU  - Saičić, Radomir N.
PY  - 2004
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2762
AB  - Optically pure (-)-cytoxazone was synthesized, starting from methyl p-methoxycinnamate, in six steps and in 31%, overall yield. The required anti-aminoalcohol configuration was established by combining Sharpless asymmetric aminohydroxylation with the configurational inversion of the intermediate amidoalcohol via ail oxazoline. The synthesis of (+)-epi-cytoxazone is also described. (C) 2003 Elsevier Ltd. All rights reserved.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron Letters
T1  - Stereoselective synthesis of (-)-cytoxazone and (+)-epi-cytoxazone
VL  - 45
IS  - 5
SP  - 955
EP  - 957
DO  - 10.1016/j.tetlet.2003.11.096
UR  - Kon_1563
ER  - 
@article{
author = "Milićević, Selena and Matović, Radomir and Saičić, Radomir N.",
year = "2004",
abstract = "Optically pure (-)-cytoxazone was synthesized, starting from methyl p-methoxycinnamate, in six steps and in 31%, overall yield. The required anti-aminoalcohol configuration was established by combining Sharpless asymmetric aminohydroxylation with the configurational inversion of the intermediate amidoalcohol via ail oxazoline. The synthesis of (+)-epi-cytoxazone is also described. (C) 2003 Elsevier Ltd. All rights reserved.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron Letters",
title = "Stereoselective synthesis of (-)-cytoxazone and (+)-epi-cytoxazone",
volume = "45",
number = "5",
pages = "955-957",
doi = "10.1016/j.tetlet.2003.11.096",
url = "Kon_1563"
}
Milićević, S., Matović, R.,& Saičić, R. N.. (2004). Stereoselective synthesis of (-)-cytoxazone and (+)-epi-cytoxazone. in Tetrahedron Letters
Oxford : Pergamon-Elsevier Science Ltd., 45(5), 955-957.
https://doi.org/10.1016/j.tetlet.2003.11.096
Kon_1563
Milićević S, Matović R, Saičić RN. Stereoselective synthesis of (-)-cytoxazone and (+)-epi-cytoxazone. in Tetrahedron Letters. 2004;45(5):955-957.
doi:10.1016/j.tetlet.2003.11.096
Kon_1563 .
Milićević, Selena, Matović, Radomir, Saičić, Radomir N., "Stereoselective synthesis of (-)-cytoxazone and (+)-epi-cytoxazone" in Tetrahedron Letters, 45, no. 5 (2004):955-957,
https://doi.org/10.1016/j.tetlet.2003.11.096 .,
Kon_1563 .

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