Approaches to the Formation of the Key 2-Oxabicyclo[3.3.0]-octan-3-one Precursor of Galiellalactone

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Abstract

New vicinal all-cis-trisubstituted derivatives of cyclopentane- and cyclopentene-containing triols were synthesized.

About the authors

A. M. Gimazetdinov

Ufa Institute of Chemistry UFRS RAS

Author for correspondence.
Email: gimazetdinov@anrb.ru
ORCID iD: 0000-0002-8539-3442
Russian Federation, prosp. Oktyabrya, 71, Ufa, 450054

V. V. Zagitov

Ufa Institute of Chemistry UFRS RAS

Email: gimazetdinov@anrb.ru
Russian Federation, prosp. Oktyabrya, 71, Ufa, 450054 Russia

Z. R. Makaev

Ufa Institute of Chemistry UFRS RAS

Email: gimazetdinov@anrb.ru
ORCID iD: 0000-0002-0958-3164
Russian Federation, prosp. Oktyabrya, 71, Ufa, 450054

References

  1. Злокачественные новообразования в России в 2021 году (заболеваемость и смертность). Ред. Каприн А.Д. и др. М.: МНИОИ им. П.А. Герцена филиал ФГБУ “НМИЦ радиологии” Минздрава России. 2022, ISBN 978-5-85502-280-33
  2. Corrie P.G. Medicine. 2008, 36, 24–28. Debnath B., Xu S., Neamati N. J. Med. Chem. 2012, 55, 6645–6668. Yu H., Lee H., Herrmann A., Buettner R., Jove R. Nat. Rev. Cancer. 2014, 14, 736–746. https://www.nature.com/articles/nrc3818.
  3. Weidler M., Rether J., Anke T., Erkel G. FEBS Lett. 2000, 484, 1–6. doi: 10.1016/S0014-5793(00)02115-3
  4. Hautzel R., Anke H. Naturforsch. 1990, 45, 1093–1098. doi: 10.18632/oncotarget.6606
  5. Koepcke B., Johansson M., Sterner O., Anke H. (2002) J. Antibiot. 2002, 55, 36–40. doi: 10.7164/antibiotics.55.36
  6. Escobar Z., Williams H., Phipps R., Karunakaran D., Steele J., Sterner O. Phytochem. Lett. 2015, 12, 138–141. doi: 10.1016/j.phytol.2015.03.009
  7. Johansson M., Koepcke B., Anke H., Sterner O. J. Antibiot. 2002, 55, 104–106. doi: 10.7164/antibiotics.55.104
  8. Nussbaum F.V., Hanke R., Fahrig T., Benet-Buchholz J. Eur. J. Org. Chem. 2004, 13, 2783–2790. doi: 10.1002/ejoc.200400137
  9. Johansson M., Sterner O. Org. Lett. 2001, 3, 2843–2845. doi: 10.1021/ol016286+
  10. Canesin G., Maggio V., Palominos M., Stiehm A., Contreras H.R., Castellón E.A., Morote J., Paciucci R., Maitland N.J., Bjartell A., Hellsten R. Sci. Rep. 2020, 10, 1–12. doi: 10.1038/s41598-020-70948-5
  11. Hellsten R., Johansson M., Dahlman A., Sterner O., Bjartell A. PLoS ONE. 2011, 6, e22118. doi: 10.1371/journal.pone.0022118
  12. Rudolph K., Serwe A., Erkel G. Cytokine. 2013, 61, 285–296. doi: 10.1016/j.cyto.2012.10.011
  13. Zhang Q., Feng Y., Kennedy D. Cell. Mol. Life Sci. 2017, 74, 777–801. doi: 10.1007/s00018-016-2362-3
  14. Hausding M., Tepe M., Übel C., Lehr H.A., Röhrig B., Höhn Y., Pautz A., Eigenbrod T., Anke T., Kleinert H., Erkel G., Finotto S. Int. Immunol. 2011, 23, 1–15. doi: 10.1093/intimm/dxq451
  15. Bollmann F., Jäckel S., Schmidtke L., Schrick K., Reinhardt C., Jurk K., Wu Z., Xia N., Li H., Erkel G., Walter U., Kleinert H., Pautz A. PLoS ONE. 2015, 10, e0130401. -doi: 10.1371/journal.pone.0130401
  16. Pérez M., Soler-Torronteras R., Collado J.A., Limones C.G., Hellsten R., Johansson M., Sterner O., Bjar-tell A., Calzado M.A., Muñoz E. Chem. Biol. Interact. 2014, 214, 69–76. doi: 10.1016/j.cbi.2014.02.012
  17. Weidler M., Rether J., Anke T., Erkel G. FEBS Lett. 2014, 484, 1–6. doi: 10.1016/S0014-5793(00)02115-3
  18. Busker S., Page B., Arnér E.S. Redox. Biol. 2020, 36, 101646. doi: 10.1016/j.redox.2020.101646
  19. Garrido-Rodríguez M., Ortea I., Calzado M.A., Muñoz E., García V. J. Proteomics. 2019, 193, 217–229. doi: 10.1016/j.jprot.2018.10.012
  20. Hellsten R., Johansson M., Dahlman A., Dizeyi N., Sterner O., Bjartell A. Prostate. 2008, 68, 269–280. doi: 10.1002/pros.20699
  21. Johansson M., Köpcke B., Anke H., Sterner O. Angew. Chem. Int. Ed. 2002, 41, 2158–2160. doi: 10.1002/1521-3773(20020617)41:12%3c2158::AID-ANIE2158%3e3.0.CO;2-P
  22. Johansson M., Köpcke B., Anke H., Sterner O. Tetrahedron. 2002, 58, 2523–2528. doi: 10.1016/S0040-4020(02)00134-5
  23. Kim T., Han Y.T., An H., Kim K., Lee J., Suh Y.G. J. Org. Chem. 2015, 80, 12193–12200. doi: 10.1021/acs.joc.5b02121
  24. Lu Y., Zhao S., Zhou S., Chen S.C., Luo T. Org. Biomol. Chem. 2019, 17, 1886–1892. doi: 10.1039/C8OB01915K
  25. Gidlöf R., Johansson M., Sterner O. Org. Lett. 2010, 12, 5100–5103. doi: 10.1021/ol101989m
  26. Kim H.S., Kim T., Ko H., Lee J., Kim Y.S., Suh Y.G. Bioorg. Med. Chem. 2017, 25, 5032–5040. doi: 10.1016/j.bmc.2017.06.036
  27. Johansson M., Sterner O. Ам. заявка US 10781197B2, 2020-09-22. https://patents.google.com/patent/US10781197B2/en
  28. Gimazetdinov A.M., Gimazetdinova T.V., Miftakhov M.S. Mendeleev Commun. 2010, 20, 15–16. doi: 10.1016/j.mencom.2010.01.006
  29. Gimazetdinov A.M., Gataullin S.S., Bushmarinov I.S., Miftakhov M.S. Tetrahedron. 2012, 68, 5754–5758. doi: 10.1016/j.tet.2012.05.036
  30. Gimazetdinov A.M., Al’mukhametov A.Z., Miftakhov M.S. New J. Chem. 2022, 46, 6708–6714. doi: 10.1039/d2nj01003h
  31. Gimazetdinov A.M., Al’mukhametov A.Z., Loza V.V., Spirikhin L.V., Miftakhov M.S. Mendeleev Commun. 2018, 28, 546–547. doi: 10.1016/j.mencom.2018.09.033

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