Home / Publications / Formal synthesis of J-type prostaglandins based on enantiopure polyfunctional cyclopentenol derivative

Formal synthesis of J-type prostaglandins based on enantiopure polyfunctional cyclopentenol derivative

Airat Maratovich Gimazetdinov 1
Airat Maratovich Gimazetdinov
, 
Aidar Zufarovich Al'mukhametov 1
Aidar Zufarovich Al'mukhametov
, 
Vadim Venerovich Zagitov 1
Vadim Venerovich Zagitov
, 
Mansur Sagar'yarovich Miftakhov 1
Mansur Sagar'yarovich Miftakhov
10.1016/j.mencom.2021.03.031
Published 2021-03-03
Communication , Volume 31, Issue 2, 239-241
3
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Gimazetdinov A. M. et al. Formal synthesis of J-type prostaglandins based on enantiopure polyfunctional cyclopentenol derivative // Mendeleev Communications. 2021. Vol. 31. No. 2. pp. 239-241.
GOST all authors (up to 50) Copy
Gimazetdinov A. M., Al'mukhametov A. Z., Zagitov V. V., Miftakhov M. S. Formal synthesis of J-type prostaglandins based on enantiopure polyfunctional cyclopentenol derivative // Mendeleev Communications. 2021. Vol. 31. No. 2. pp. 239-241.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2021.03.031
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.031
TI - Formal synthesis of J-type prostaglandins based on enantiopure polyfunctional cyclopentenol derivative
T2 - Mendeleev Communications
AU - Gimazetdinov, Airat Maratovich
AU - Al'mukhametov, Aidar Zufarovich
AU - Zagitov, Vadim Venerovich
AU - Miftakhov, Mansur Sagar'yarovich
PY - 2021
DA - 2021/03/03
PB - Mendeleev Communications
SP - 239-241
IS - 2
VL - 31
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2021_Gimazetdinov,
author = {Airat Maratovich Gimazetdinov and Aidar Zufarovich Al'mukhametov and Vadim Venerovich Zagitov and Mansur Sagar'yarovich Miftakhov},
title = {Formal synthesis of J-type prostaglandins based on enantiopure polyfunctional cyclopentenol derivative},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.031},
number = {2},
pages = {239--241},
doi = {10.1016/j.mencom.2021.03.031}
}
MLA
Cite this
MLA Copy
Gimazetdinov, Airat Maratovich, et al. “Formal synthesis of J-type prostaglandins based on enantiopure polyfunctional cyclopentenol derivative.” Mendeleev Communications, vol. 31, no. 2, Mar. 2021, pp. 239-241. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.031.

Keywords

15d-prostaglandin J2
cyclopropanation
macrolactonization
silyl migration
Wittig reaction

Abstract

The Wittig reaction of {(1S,4R,5R)-5-[(tert-butyldimethylsilyloxy) methyl]-4-hydroxycyclopent-2-en-1-yl}acetaldehyde is accompanied by the migration of silyl protective group from the primary hydroxy group to the secondary one, which enables further synthesis of J-type prostaglandins. Study of this phenomemon on model relative ester comprising base variation revealed formation of unusual functionalized bicyclo[3.1.0]hex-2-ene-6-carboxylate derivative.

References

3.
The Eicosapentaenoic Acid Metabolite 15-Deoxy-δ12,14-Prostaglandin J3 Increases Adiponectin Secretion by Adipocytes Partly via a PPARγ-Dependent Mechanism
Lefils-Lacourtablaise J., Socorro M., Géloën A., Daira P., Debard C., Loizon E., Guichardant M., Dominguez Z., Vidal H., Lagarde M., Bernoud-Hubac N.
PLoS ONE, 2013
5.
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
6.
15-Deoxy-Δ12,14-prostaglandin J2: An Electrophilic Trigger of Cellular Responses
Uchida K., Shibata T.
Chemical Research in Toxicology, 2007
9.
Cross-Conjugated Cyclopentenone Prostaglandins. Recent Advances
Loza V.V., Gimazetdinov A.M., Miftakhov M.S.
Russian Journal of Organic Chemistry, 2018
10.
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
11.
Enantioselective Synthesis of 15-Deoxy-Δ12,14-Prostaglandin J2
Li J., Stoltz B.M., Grubbs R.H.
Organic Letters, 2019
12.
Short Total Synthesis of Δ12-Prostaglandin J2 and Related Prostaglandins. Design, Synthesis, and Biological Evaluation of Macrocyclic Δ12-Prostaglandin J2 Analogues
Nicolaou K.C., Pulukuri K.K., Rigol S., Peitsinis Z., Yu R., Kishigami S., Cen N., Aujay M., Sandoval J., Zepeda N., Gavrilyuk J.
Journal of Organic Chemistry, 2018
13.
B. K. Goering, PhD Thesis, Cornell University, 1995.
16.
Al’mukhametov A.Z., Gimazetdinov A.M., Miftakhov M.S.
Mendeleev Communications, 2020
18.
Gimazetdinov A.M., Almukhametov A.Z., Loza V.V., Spirikhin L.V., Miftakhov M.S.
Mendeleev Communications, 2018
19.
10.1016/j.mencom.2021.03.031_bib0095
Greene
Greene's Protective Groups in Organic Synthesis, 2007
21.
10.1016/j.mencom.2021.03.031_bib0105
Jones
J. Chem. Soc., Perkin Trans., 1979
22.
The self-condensation reaction of lithium ester enolates. Isolation of a ketene intermediate
Sullivan D.F., Woodbury R.P., Rathke M.W.
Journal of Organic Chemistry, 1977