One-pot synthesis of cyclic β-dicarbonyl compounds as synthons for 11-deoxyprostanoids
https://doi.org/10.29235/1561-8323-2020-64-2-186-192
Abstract
One-pot synthesis of cyclic β-dicarbonyl synthons for 11-deoxyprostanoids has been developed on the basis of cyclopentane-1,3-dione and 5-phenyl tetronic acid. The obtained 2-alkyl(arylalkyl)-substituted cyclopentane-1,3-diones have been transformed into cyclopentenone precursors of 11-deoxy-PGE 1 and 11-deoxy-PGE 2 analogues.
Keywords
cyclopentane-1,3-dione,
5-phenyl tetronic acid,
cyclic β-dicarbonyl compounds,
one-pot synthesis,
cyclopentenones
Supporting agencies: The study was financially supported by the Belarusian Republican Foundation for Fundamental Research (grant Х18Р-046).
About the Authors
F. S. Pashkovsky
Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Pashkovsky Felix S. – Ph. D. (Chemistry), Head of the Laboratory.
5/2, Kuprevich Str., 220141, Minsk
Yu. S. Dontsu
Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Dontsu Yuliya S. – Ph. D. (Chemistry), Senior researcher.
5/2, Kuprevich Str., 220141, Minsk
D. I. Korneev
Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Korneev Dmitry I. – Master of Chemistry, Junior researcher.
5/2, Kuprevich Str., 220141, Minsk
D. B. Rubinov
Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Rubinov Dmitry B. – Ph. D. (Chemistry), Leading researcher.
5/2, Kuprevich Str., 220141, Minsk
F. A. Lakhvich
Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Lakhvich Fedor A. – Academician, D. Sc. (Chemistry), Professor, Chief researcher.
5/2, Kuprevich Str., 220141, Minsk
References
1. Lakhvich F. A., Pashkovsky F. S., Koroleva E. V. Heteroprostanoids: synthesis and biological activity. Russian Chemical Reviews, 1992, vol. 61, no. 2, pp. 243–266. https://doi.org/10.1070/rc1992v061n02abeh000943
2. Collins P. W., Djuric S. W. Synthesis of Therapeutically Useful Prostaglandin and Prostacyclin Analogs. Chemical Reviews, 1993, vol. 93, no. 4, pp. 1533–1564. https:// doi.org/10.1021/cr00020a007
3. Biaggio F. C., Rufino A. R., Zaim M. H., Zaim C. Y. H., Bueno M. A., Rodrigues A. Synthesis and Biological Activity of Prostaglandin Analogs Containing Heteroatoms in the Cyclopentane Ring. Current Organic Chemistry, 2005, vol. 9, no. 5, pp. 419–457. https://doi.org/10.2174/1385272053174912
4. Das S., Chandrasekhar S., Yadav J. S., Grée R. Recent Developments in the Synthesis of Prostaglandins and Analogs. Chemical Reviews, 2007, vol. 107, no. 7, pp. 3286–3337. https://doi.org/10.1021/cr068365a
5. Ge Y.-Y., Cai Z.-Y., Zhou W.-C. Progress in the Total Synthesis of Prostaglandins. Chinese Journal of Pharmaceuticals, 2013, vol. 44, no. 7, pp. 720–728.
6. Peng H., Chen F.-E. Recent advances in asymmetric total synthesis of prostaglandins. Organic and Biomolecular Chemistry, 2017, vol. 15, no. 30, pp. 6281–6301. https://doi.org/10.1039/c7ob01341h
7. Dams I., Wasyluk J., Prost M., Kutner A. Therapeutic uses of prostaglandin F 2α analogues in ocular disease and novel synthetic strategies. Prostaglandins & Other Lipid Mediators, 2013, vol. 104–105, pp. 109–121. https://doi.org/10.1016/j.prostaglandins.2013.01.001
8. Khlebnicova T. S., Lakhvich F. A. Synthesis of natural and related bioactive substances based on derivatives of cyclic b-diketones. Itogi i perspektivy razvitiya bioorganicheskoi khimii v Respublike Belarus’: sbornik statei, posvyashchyashchennykh 85-letiyu akademika A. A. Akhrema [Results and prospects for the development of bioorganic chemistry in the Republic of Belarus: collection articles dedicated to 85th anniversary of Academician A. A. Akhrem]. Grodno, 1998, pp. 157–182 (in Russian).
9. Schmidt A., Boland W. General Strategy for the Synthesis of B 1 Phytoprostanes, Dinor Isoprostanes, and Analogs. Journal of Organic Chemistry, 2007, vol. 72, no. 5, pp. 1699–1706. https://doi.org/10.1021/jo062359x
10. Pashkovskii F. S., Katok Ya. M., Khlebnikova T. S., Koroleva E. V., Lakhvich F. A. Heterocyclic analogs of prostaglandins. I. Synthesis of 3-alkyl(aralkyl)-2,5-dihydrofuran-2-ones as synthons for 11-deoxy-10-oxaprostanoids. Russian Journal of Organic Chemistry, 2003, vol. 39, no. 7, pp. 998–1009. https://doi.org/10.1023/b:rujo.0000003193.75790.de
11. Pashkovskii F. S., Shchukina E. M., Gribovskii M. G., Lakhvich F. A. Heterocyclic analogs of prostaglandins. IV. Synthesis of 3,7-interphenylene 3,10(11)-dioxa-13-azaprostanoids and 9-oxa-7-azaprostanoids based on tetronic acid and aromatic aldehydes. Russian Journal of Organic Chemistry, 2008, vol. 44, no. 5, pp. 657–670. https://doi.org/10.1134/s1070428008050047
12. Hayashi Y. Pot economy and one-pot synthesis. Chemical Science, 2016, vol. 7, no. 2, pp. 866–880. https://doi.org/10.1039/c5sc02913a
13. Sydnes M. O. One-Pot Reactions: A Step Towards Greener Chemistry. Current Green Chemistry, 2014, vol. 1, no. 3, pp. 216–226. https://doi.org/10.2174/2213346101666140221225404
14. Pashkovsky F. S., Korneev D. I., Lakhvich F. A. Synthons for new 11-deoxy-3-oxa-3,7-inter-m-phenylene prostaglandin analogues. Doklady Natsional’noi akademii nauk Belarusi = Doklady of the National Academy of Sciences of Belarus, 2019, vol. 63, no. 3, pp. 291–297 (in Russian). https://doi.org/10.29235/1561-8323-2019-63-3-291-297
Review
Views: 784
Email this article 