Synthesis of (3 aS ,4 aS ,6 aR )-2-oxo-3,3 a ,4,6 a -tetrahydro-2 H -cyclopenta[b]furan-4-yl acetate, as a key synthon in approaches to (–)-galiellalactone

A. M. Gimazetdinov; Гимазетдинов Айрат Маратович; V. V. Zagitov; Загитов В. В.; Z. R. Makaev; Макаев Зайнутдин Рамилевич; M. S. Miftakhov; Мифтахов М. С.

doi:10.31857/S0514749225020062

Synthesis of (3aS,4aS,6aR)-2-oxo-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-4-yl acetate, as a key synthon in approaches to (–)-galiellalactone

Авторлар: Gimazetdinov A.M.¹, Zagitov V.V.¹, Makaev Z.R.¹, Miftakhov M.S.¹
Мекемелер:
1. Ufa Institute of Chemistry UFRS RAS
Шығарылым: Том 61, № 2 (2025)
Беттер: 167-171
Бөлім: Articles
URL: https://permmedjournal.ru/0514-7492/article/view/684320
DOI: https://doi.org/10.31857/S0514749225020062
EDN: https://elibrary.ru/DGQXMT
ID: 684320

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат
Рұқсат жабық

Рұқсат берілді
Рұқсат жабық

Тек жазылушылар үшін

Аннотация
Толық мәтін
Авторлар туралы
Әдебиет тізімі
Қосымша файлдар
Статистика

Аннотация

The synthesis of bicyclic allyl acetate 2, a promising precursor of (-)-galileolactone 1, is described. The approach is based on the separation of diastereomeric carboxamides obtained by amidation of racemic gem-dichloro-substituted Grieco lactone with (+)-α-methylbenzylamine. Subsequent steps of transformation of an individual diastereomer include reactions of complete reductive dechlorination, construction of an allyl alcohol fragment in the ring part by stereo- and regiospecific bromohydroxylylation with NBS in aqueous THF, and dehydrobromination.

Негізгі сөздер

bicyclic γ-lactones, galliellalactones, bromohydroxylation, haloiminolactonization, (+)-α-methylbenzylamine, Grieco lactone

Толық мәтін

Әдебиет тізімі

Hautzel R., Anke H. Naturforsch. 1990, 45, 1093–1098. doi: 10.18632/oncotarget.6606
Koepcke B., Johansson M., Sterner O., Anke H. J. Antibiot. 2002, 55, 36–40. doi: 10.7164/antibiotics.55.36
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
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
Hellsten R., Johansson M., Dahlman A., Sterner O., Bjartell A. PLoS One. 2011, 6, e22118. doi: 10.1371/journal.pone.0022118
Rudolph K., Serwe A., Erkel G. Cytokine. 2013, 61, 285–296. doi: 10.1016/j.cyto.2012.10.011
Zhang Q., Feng Y., Kennedy D. Cell. Mol. Life Sci. 2017, 74, 777–801. doi: 10.1007/s00018-016-2362-3
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
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
Pérez M., Soler-Torronteras R., Collado J.A., Limones C.G., Hellsten R., Johansson M., Sterner O., Bjartell A., Calzado M.A., Muñoz E. Chem. Biol. Interact. 2014, 214, 69–76. doi: 10.1016/j.cbi.2014.02.012
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
Gimazetdinov A.M., Vostrikov N.S., Miftakhov M.S. Tetrahedron: Asymmetry. 2008, 19, 1094–1099. doi: 10.1016/j.tetasy.2008.04.001
Loza V.V., Valiullina Z.R., Miftakhov M.S. Russ. Chem. Bull. 2021, 70, 1–31. doi: 10.1007/s11172-021-3052-3
Valiullina Z.R., Akhmetyanova V.A., Ivanova N.A., Miftakhov M.S. Tetrahedron Lett. 2015, 56, 6904–6907. doi: 10.1016/j.tetlet.2015.10.106
Tello-Aburto R., Rios M.Y., Swenson D.C., Olivo H.F. Tetrahedron Lett. 2008, 49, 6853-6855. doi: 10.1016/j.tetlet.2008.09.081
Johansson M., Sterner O. Org. Lett. 2001, 3, 2843–2845.doi: 10.1021/ol016286+