Method for Synthesis of (±)-Entecavir

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Abstract

Starting from (±)-lactonediol Corey, a practical route for the synthesis of (±)-Entecavir was developed, the key step of which is the preparation of (1R*,3R*,4S*)-4-(1-ethoxyethoxy)-3-[(1-ethoxyethoxy) methyl]-2-methylenecyclopentanol by oxidative decarboxylation of {(1S*,2R*,3S*,5R*)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-(1-ethoxyethoxy)-2-[(1-ethoxyethoxy)methyl]cyclopentyl}acetic acid with lead tetraacetate.

About the authors

Z. R. Valiullina

Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences (UFRC RAS)

Email: valiullina.zulya@mail.ru
prosp. Oktyabrya, 69, Ufa, 450054 Russia

N. A. Ivanova

Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences (UFRC RAS)

prosp. Oktyabrya, 69, Ufa, 450054 Russia

M. S. Miftakhov

Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences (UFRC RAS)

prosp. Oktyabrya, 69, Ufa, 450054 Russia

References

  1. Suzuki K., Suda G., Yamamoto Y., Furuya K., Baba M., Kimura M., Maehara O., Shimazaki T, Yamamoto K., Shigesawa T., Nakamura A., Ohara M., Kawagishi N., Nakai M., Sho T., Natsuizaka M., Morikawa K., Oga- wa K., Sakamoto N. Hepatol. Res. 2019, 49, 1294–1304. doi: 10.1111/hepr.13399
  2. Crimmins M.T., King B.W. J. Org. Chem. 1996, 61, 4192–4193. doi: 10.1021/jo960708p
  3. Faletto M.B., Miller W.H., Garvey E.P., Clair M.H. St., Daluge S.M., Good S.S. Antimicrob. Agents Chemother. 1997 41, 1099–1107. doi: 10.1128/aac.41.5.1099
  4. Innaimo S.F., Seifer M., Bisacchi G.S., Standring D.N., Zahler R., Colonno R. J. Antimicrob. Agents Chemother. 1997, 41, 1444–1448. doi: 10.1128/aac.41.7.1444
  5. Campian M., Putala M., Sebesta R. Curr. Org. Chem. 2014, 18, 2808–2832.
  6. Hyun Y.E., Kim H.R., Choi Y., Jeong L. S. Asian J. Org. Chem. 2017, 6, 1213–1218. doi: 10.1002/ajoc.201700032.
  7. Velasco J., Ariza X., Badía L., Bartra M., Berenguer R., Farràs J., Gallardo J., Garcia J., Gasanz Y. J. Org. Chem. 2013, 78, 5482−5491. doi: 10.1021/jo400607v.
  8. Liu X., Jiao X., Wu Q., Tian C., Li R., Xie P. Tetrahedron Lett. 2012, 53, 3805–3807. doi: 10.1016/j.tetlet.2012.05.058.
  9. Xu H., Wang F., Xue W., Zheng Y., Wang Q., Qiu F., Jin Y. Org. Process Res. Dev. 2018, 22, 377–384. doi: 10.1021/acs.oprd.8.
  10. Liu L., Sun Y., Wang J., Ou W., Wang X., Huang S. Synlett. 2019, 30, 748–752. doi: 10.1055/s-0037-1612215
  11. Wang S., Zhang X., Gu H., Zhu X., Guo Y. Org. Preparations Procedures International, 2017, 49, 568–574. doi: 10.1080/00304948.2017.1384284
  12. Vostrikov N.S., Lobko I.F, Valiullina Z.R. Mifta- khov M.S Mendeleev Commun. 2017, 27, 12–13. doi: 10.1016/j.mencom.2017.01.002
  13. Толстиков Г.А., Мифтахов М.С., Валеев Ф.А., Востриков Н.С., Ахметвалеев Р.Р. ЖОрХ. 1984, 20, 221–222. [Tolstikov G.A., Miftakhov M.S., Valeev F.A., Vostrikov N.S., Akhmetvaleev R.R., Zh. Org. Khim. 1984. 20, 221–222.]
  14. Гордон А., Форд Р. Спутник химика. М.: Мир, 1976, 542.

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