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
,
Elena Rozhkova
4
,
Mikhail Maslov
2
,
Nataliya V Groza
2
,
Н. Ф. Мясоедов
3
,
Hartmut Kuhn
1
,
Galina I. Myagkova
2
1
3
Publication type: Journal Article
Publication date: 2003-10-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 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.
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Total citations:
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Citations from 2024:
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GOST
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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.
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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.
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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 -
Cite this
BibTex (up to 50 authors)
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@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}
}
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.
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