volume 59 issue 41 pages 8091-8097

A convergent synthesis of (17R,5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid analogues and their tritiated derivatives

Igor Ivanov 1
Stepan G. Romanov 2
Valery Shevchenko 3
Nataliya V Groza 2
Н. Ф. Мясоедов 3
Hartmut Kuhn 1
Galina I. Myagkova 2
Publication typeJournal Article
Publication date2003-10-01
scimago Q3
wos Q2
SJR0.426
CiteScore4.1
Impact factor2.2
ISSN00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
17(R)-OH-AA and 14,15-dehydro-17(R)-OH-AA were synthesized from a common tetraacetylenic precursor and their azide derivatives were obtained in moderate yields via the corresponding p-toluenesulfonates. Since the azido group remained stable during tritiation procedure on Lindlar's catalyst in benzene, both 14,15-dehydro-17(S)-N3-AA and 14,15-dehydro-17(R)-OH-AA constitute useful intermediates in the synthesis of radio-labelled 17(S)-N3-AA and 17(R)-OH-AA. In contrast, reduction of azide in methanol afforded 17(S)-NH2-AA with 95% yield.
Found 
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Romanov S. G. et al. A convergent synthesis of (17R,5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid analogues and their tritiated derivatives // Tetrahedron. 2003. Vol. 59. No. 41. pp. 8091-8097.
GOST all authors (up to 50) Copy
Ivanov I., Romanov S. G., Shevchenko V., Rozhkova E., Maslov M., Groza N. V., Мясоедов Н. Ф., Kuhn H., Myagkova G. I. A convergent synthesis of (17R,5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid analogues and their tritiated derivatives // Tetrahedron. 2003. Vol. 59. No. 41. pp. 8091-8097.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1016/j.tet.2003.08.043
UR - https://linkinghub.elsevier.com/retrieve/pii/S0040402003013371
TI - A convergent synthesis of (17R,5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid analogues and their tritiated derivatives
T2 - Tetrahedron
AU - Ivanov, Igor
AU - Romanov, Stepan G.
AU - Shevchenko, Valery
AU - Rozhkova, Elena
AU - Maslov, Mikhail
AU - Groza, Nataliya V
AU - Мясоедов, Н. Ф.
AU - Kuhn, Hartmut
AU - Myagkova, Galina I.
PY - 2003
DA - 2003/10/01
PB - Elsevier
SP - 8091-8097
IS - 41
VL - 59
SN - 0040-4020
SN - 1464-5416
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2003_Romanov,
author = {Igor Ivanov and Stepan G. Romanov and Valery Shevchenko and Elena Rozhkova and Mikhail Maslov and Nataliya V Groza and Н. Ф. Мясоедов and Hartmut Kuhn and Galina I. Myagkova},
title = {A convergent synthesis of (17R,5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid analogues and their tritiated derivatives},
journal = {Tetrahedron},
year = {2003},
volume = {59},
publisher = {Elsevier},
month = {oct},
url = {https://linkinghub.elsevier.com/retrieve/pii/S0040402003013371},
number = {41},
pages = {8091--8097},
doi = {10.1016/j.tet.2003.08.043}
}
MLA
Cite this
MLA Copy
Romanov, Stepan G., et al. “A convergent synthesis of (17R,5Z,8Z,11Z,14Z)-17-hydroxyeicosa-5,8,11,14-tetraenoic acid analogues and their tritiated derivatives.” Tetrahedron, vol. 59, no. 41, Oct. 2003, pp. 8091-8097. https://linkinghub.elsevier.com/retrieve/pii/S0040402003013371.