Home / Publications / A facile synthesis of (±)-15-deoxy-Δ12,14-prostaglandin J2 methyl ester

A facile synthesis of (±)-15-deoxy-Δ12,14-prostaglandin J2 methyl ester

Zaynutdin Ramilevich Makaev 1
Zaynutdin Ramilevich Makaev
, 
Nikolay Sergeyevich Vostrikov 1
Nikolay Sergeyevich Vostrikov
, 
Natalya Kazimirovna Selezneva 1
Natalya Kazimirovna Selezneva
, 
Mansur Sagar'yarovich Miftakhov 1
Mansur Sagar'yarovich Miftakhov
1 Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation
10.1016/j.mencom.2023.06.012
Published 2023-06-13
Communication , Volume 33, Issue 4, 479-480
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Makaev Z. R. et al. A facile synthesis of (±)-15-deoxy-Δ12,14-prostaglandin J2 methyl ester // Mendeleev Communications. 2023. Vol. 33. No. 4. pp. 479-480.
GOST all authors (up to 50) Copy
Makaev Z. R., Vostrikov N. S., Selezneva N. K., Miftakhov M. S. A facile synthesis of (±)-15-deoxy-Δ12,14-prostaglandin J2 methyl ester // Mendeleev Communications. 2023. Vol. 33. No. 4. pp. 479-480.
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TY - JOUR
DO - 10.1016/j.mencom.2023.06.012
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.012
TI - A facile synthesis of (±)-15-deoxy-Δ12,14-prostaglandin J2 methyl ester
T2 - Mendeleev Communications
AU - Makaev, Zaynutdin Ramilevich
AU - Vostrikov, Nikolay Sergeyevich
AU - Selezneva, Natalya Kazimirovna
AU - Miftakhov, Mansur Sagar'yarovich
PY - 2023
DA - 2023/06/13
PB - Mendeleev Communications
SP - 479-480
IS - 4
VL - 33
ER -
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@article{2023_Makaev,
author = {Zaynutdin Ramilevich Makaev and Nikolay Sergeyevich Vostrikov and Natalya Kazimirovna Selezneva and Mansur Sagar'yarovich Miftakhov},
title = {A facile synthesis of (±)-15-deoxy-Δ12,14-prostaglandin J2 methyl ester},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.012},
number = {4},
pages = {479--480},
doi = {10.1016/j.mencom.2023.06.012}
}
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Makaev, Zaynutdin Ramilevich, et al. “A facile synthesis of (±)-15-deoxy-Δ12,14-prostaglandin J2 methyl ester.” Mendeleev Communications, vol. 33, no. 4, Jun. 2023, pp. 479-480. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.012.

Keywords

14-prostaglandin J2
15-deoxyΔ12
Corey lactone diol
dehydration
diastereoselective reaction
dienes.
prostaglandin J2 methyl ester

Abstract

A simple and facile synthesis of racemic 15-deoxy-Δ12,14-prostaglandin J2 methyl ester from readily available Corey lactone diol in total eleven steps was suggested. The standard methods provided a pathway to a block with an integrated w w w-chain and further to PGJ2 methyl ester. The latter was smoothly converted to the target prostaglandin in the TsOH-CH2Cl2 medium when allylic alcohol moiety was transformed to exocyclic diene substituent conjugated with endocyclic enone system.

References

.
Concise and enantioselective total synthesis of 15-deoxy-Δ-(12,14)-prostaglandin J(2).
Kim N., Moon H., Park T., Yun H., Jung J., Chang D., Kim D., Suh Y.
Journal of Organic Chemistry, 2010
.
Chemical Implications for Antitumor and Antiviral Prostaglandins:  Reaction of Δ7-Prostaglandin A1 and Prostaglandin A1 Methyl Esters with Thiols
Suzuki M., Mori M., Niwa T., Hirata R., Furuta K., Ishikawa T., Noyori R.
Journal of the American Chemical Society, 1997
.
First Enantioselective Total Synthesis of (8S,12R,15S)-Prostaglandin J2
Zanoni G., Porta A., De Toma Q., Castronovo F., Vidari G.
Journal of Organic Chemistry, 2003
.
Cyclopentenone Prostaglandin, 15-Deoxy-Δ12,14-PGJ2, Is Metabolized by HepG2 Cells via Conjugation with Glutathione
Brunoldi E.M., Zanoni G., Vidari G., Sasi S., Freeman M.L., Milne G.L., Morrow J.D.
Chemical Research in Toxicology, 2007
.
Total Synthesis of Prostaglandin 15d-PGJ2 and Investigation of its Effect on the Secretion of IL-6 and IL-12
Egger J., Fischer S., Bretscher P., Freigang S., Kopf M., Carreira E.M.
Organic Letters, 2015
.
Concise Syntheses of Δ12-Prostaglandin J Natural Products via Stereoretentive Metathesis
Li J., Ahmed T.S., Xu C., Stoltz B.M., Grubbs R.H.
Journal of the American Chemical Society, 2018
.
Cross-Conjugated Cyclopentenone Prostaglandins. Recent Advances
Loza V.V., Gimazetdinov A.M., Miftakhov M.S.
Russian Journal of Organic Chemistry, 2018
.
Synthesis of (±)-15-deoxy-Δ12,14-prostaglandin J2 and Δ12-prostaglandin J2 15-acetate methyl esters
Vostrikov N.S., Lobko I.F., Ishimova D.U., Miftakhov M.S.
Russian Journal of Organic Chemistry, 2015
.
The conjugate addition–Peterson olefination reaction for the preparation of cross-conjugated cyclopentenone, PPAR-γ ligands
Iqbal M., Duffy P., Evans P., Cloughley G., Allan B., Lledó A., Verdaguer X., Riera A.
Organic and Biomolecular Chemistry, 2008
.
Synthesis and use of 7-substituted norbornadienes for the preparation of prostaglandins and prostanoids
Baxter A.D., Binns F., Javed T., Roberts S.M., Sadler P., Scheinmann F., Wakefield B.J., Lynch M., Newton R.F.
Journal of the Chemical Society Perkin Transactions 1, 1986