Synthesis of 4,6-disubstituted bicyclo[3.3.1]nona-3,6-dien-2-ones

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Аннотация

Bicyclo[3.3.1]nonane system is an important structural motif observed in a diverse natural products. Here, we report a concise synthetic route exploiting aldol condensation reactions for construction bicyclo[3.3.1]nonane ring system. Our strategy employes cyclohex-2-enones bearing another carbonyl group in side chain as key structural unit. The reaction showed good results for substrates bearing electron-donating groups in aromatic substituents. Overall, the described synthesis of bicyclo[3.3.1]nona-3,6-dien-2-ones required 2 steps and only 2 building blocks (such as Mannich base and acetoacetic ester) to access desired bicyclic system.

Авторлар туралы

S. Mikhalyonok

Belarusian State Technological University

V. Bezborodov

Belarusian State Technological University

N. Kuz'menok

Belarusian State Technological University

A. Savelyev

Belarusian State Technological University

A. Arol

Belarusian State Technological University

Email: olegek993@gmail.com

Әдебиет тізімі

  1. Takashima, J., Ohsaki, A. J. Nat. Prod. 2001, 64, 1493-1496. doi: 10.1021/np010389j
  2. Amagata, T., Tanaka, M., Yamada, T., Minoura, K., Numata, A. J. Nat. Prod. 2008, 71, 1493340-1493345. doi: 10.1021/np070529a
  3. Wu Q., Li S.-W., Xu H., Wang H., Hu P., Zhang H., Luo C., Chen K.-X., Nay B., Guo Y.-W., Li X.-W. Angew. Chem. Int. Ed. 2020, 59, 12105-12112. doi: 10.1002/anie.202003643
  4. Duan Y., Hu P., Guo Y., Bu P., Shi Z., Cao Y., Zhang Y., Hu H., Tong Q., Qi C. Phytochemistry. 2022, 199, 113166. doi: 10.1016/j.phytochem.2022.113166
  5. Shen X., Ting C.P., Xu G., Maimone T.J. Nat. Commun. 2020, 11, Art. 508. doi: 10.1038/s41467-020-14354-5
  6. Jones K.E., Park B., Doering N.A., Baik M.-H., Sarpong R. J. Am. Chem. Soc. 2021, 143, 20482-20490. doi: 10.1021/jacs.1c10804
  7. Sanchez A., Maimone T.J. J. Am. Chem. Soc. 2022, 144, 7594-7599. doi: 10.1021/jacs.2c02627
  8. Ji Y., Hong B., Franzoni I., Wang M., Guan W., Jia H., Li H. Angew. Chem. Int. Ed. 2022, 61, e202116136. doi: 10.1002/anie.202116136
  9. Daube W.G., McFarland J.W. J. Am. Chem. Soc. 1960, 82, 4245-4248. doi: 10.1021/ja01501a032
  10. Knott P.A., Mellor J.M. J. Chem. Soc. (C). 1971, 670-674. doi: 10.1039/J39710000670
  11. Das Gupta R., Ranu B.C., Ghatak U.R. Indian J. Chem., Sect. B. 1983, 22B, 619-620.
  12. Chakraborti R., Ranu B.C., Ghatak U.R. J. Org. Chem. 1985, 50, 5268-5271. doi: 10.1021/jo00225a054
  13. Пчелинцева Н.В., Колеватова Я.Г., Маркова Л.И., Федотова О.В., Решетов П.В. 2008, ЖОрХ. 2008, 44, 1283-1286.
  14. Pchelintseva N.V., Kolevatova Ya.G., Markova L.I., Feotova O.V., Reshetov P.V. Russ. J. Org. Chem. 2008, 44, 1267-1270. doi: 10.1134/S1070428008090030
  15. Zhao Y.-L., Chen L., Yang S.-C., Tian C., Liu Q. J. Org. Chem. 2009, 74, 5622-5625. doi: 10.1021/jo900764s
  16. Crotti P., Macchia F. Gazz. Chim. Ital. 1970, 100, 999-1011.
  17. Carpio H., Rooks W.H., Crabbe P. J. Med. Chem. 1970, 13, 634-637. doi: 10.1021/jm00298a012
  18. Rao H.S.P., Rao A.V., Desai A. Proc. Natl. Acad. Sci. India Sect. A Phys. Sci. 2013, 83, 195-206. doi: 10.1007/s40010-013-0076-6
  19. Möhrle H., Platzek T., Wille R., Wendisch D. Z. Naturforsch., Teil B. 1985, 40, 524-533. doi: 10.1515/znb-1985-0415
  20. Li Z., He L., Fu R., Song G., Song W., Xie D., Yang J. Tetrahedron. 2016, 72, 4321-4328. doi: 10.1016/j.tet.2016.05.071
  21. Das B., Thirupathi P., Mahender I., Reddy K.R. J. Mol. Cat. A: Chem. 2006, 247, 182-185. doi: 10.1016/j.molcata.2005.11.044
  22. Breugst M., Heiden D. Chem. Eur. J. 2018, 24, 9187-9199. doi: 10.1002/chem.201706136
  23. Цимбаленко Д.А., Скуратова М.И., Федотова О.В., Харченко В.Г. ХГС. 1999, 35, 1688-1690.
  24. Tsimbalenko D.A., Skuratova M.I., Fedotova O.V., Kharchenko V.G. Chem. Heterocycl. Compd. 1999, 35, 1482-1483. doi: 10.1007/BF02251826
  25. Буров А.М., Пчелинцева Н.В., Федотова О.В. ХГС. 2008, 44, 1152-1159.
  26. Burov A.M., Pchelintseva N.V., Fedotova O.V. Chem. Heterocycl. Compd. 2008, 44, 924-930. doi: 10.1007/s10593-008-0134-1
  27. Wang Z., Fan G., Zeng Z., Wang X., Jiang R. Междунар. заявка WO 2019 76343. С.А. 2019, 170, 534763.
  28. Qin Y., Wang W. Пат. 105001212 (2018). КНР. С.А. 2015, 163, 649336.

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