18-iodooctadeca-(8Z,11Z)-dienoic acid as useful intermediate for the synthesis of special lipoxygenase substrates bearing bulky substituents at the ω-position
Publication type: Journal Article
Publication date: 2000-01-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
18-Iodooctadeca-(8Z,11Z)-dienoic acid (7) was synthesized in five steps starting from methyl 10-bromodec-7-ynoate (2) in an overall yield of 53%. The synthetic procedure involves Cu(I)-catalyzed cross-coupling of propargylic bromide 2 with 7-octyn-1-ol (3), followed by hydrogenation of the coupling product 4 to Z,Z-diene 5 on Lindlar's catalyst and subsequent substitution of the OH– group of 5 with iodine. Coupling of the resulting iodide 7 with low-order organic cuprates [t-Bu2CuLi or (PhCH2)2CuMgCl] leads to 19,19-dimethyleicosa-(8Z,11Z)-dienoic acid (1a) and 19-phenylnonadeca-(8Z,11Z)-dienoic acid (1b), respectively.
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7
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Groza N. V. et al. 18-iodooctadeca-(8Z,11Z)-dienoic acid as useful intermediate for the synthesis of special lipoxygenase substrates bearing bulky substituents at the ω-position // Tetrahedron. 2000. Vol. 56. No. 4. pp. 553-556.
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Ivanov I., Groza N. V., Romanov S. G., Kuhn H., Myagkova G. I. 18-iodooctadeca-(8Z,11Z)-dienoic acid as useful intermediate for the synthesis of special lipoxygenase substrates bearing bulky substituents at the ω-position // Tetrahedron. 2000. Vol. 56. No. 4. pp. 553-556.
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TY - JOUR
DO - 10.1016/S0040-4020(99)01032-7
UR - https://linkinghub.elsevier.com/retrieve/pii/S0040402099010327
TI - 18-iodooctadeca-(8Z,11Z)-dienoic acid as useful intermediate for the synthesis of special lipoxygenase substrates bearing bulky substituents at the ω-position
T2 - Tetrahedron
AU - Ivanov, Igor
AU - Groza, Nataliya V
AU - Romanov, Stepan G.
AU - Kuhn, Hartmut
AU - Myagkova, Galina I.
PY - 2000
DA - 2000/01/01
PB - Elsevier
SP - 553-556
IS - 4
VL - 56
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{2000_Groza,
author = {Igor Ivanov and Nataliya V Groza and Stepan G. Romanov and Hartmut Kuhn and Galina I. Myagkova},
title = {18-iodooctadeca-(8Z,11Z)-dienoic acid as useful intermediate for the synthesis of special lipoxygenase substrates bearing bulky substituents at the ω-position},
journal = {Tetrahedron},
year = {2000},
volume = {56},
publisher = {Elsevier},
month = {jan},
url = {https://linkinghub.elsevier.com/retrieve/pii/S0040402099010327},
number = {4},
pages = {553--556},
doi = {10.1016/S0040-4020(99)01032-7}
}
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MLA
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Groza, Nataliya V., et al. “18-iodooctadeca-(8Z,11Z)-dienoic acid as useful intermediate for the synthesis of special lipoxygenase substrates bearing bulky substituents at the ω-position.” Tetrahedron, vol. 56, no. 4, Jan. 2000, pp. 553-556. https://linkinghub.elsevier.com/retrieve/pii/S0040402099010327.
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