Synthesis of Ethyl Ester of 11-Deoxy-13,14-didehydro-17-methyl-20-norprostaglandin B1_Analog of Misoprostol

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Abstract

By 1,2-addition to the keto group ethyl-(5-oxocyclopent-1-enyl)heptenoate lithium acetylenide from 4-hydroxy-4,5-dimethylheptin-1, followed by oxidative isomerization of the resulting adduct with PCC was obtained ethyl ester 11-deoxy-13,14-didehydro-17-methyl-20-nor-prostaglandin B1.

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N. A. Ivanova

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

Author for correspondence.
Email: gushavaleeva@mail.ru
ORCID iD: 0000-0002-3101-1285
Russian Federation, prosp. Oktabrya, 71, Ufa, 450054

G. A. Shavaleeva

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

Email: gushavaleeva@mail.ru
ORCID iD: 0000-0003-1345-9139
Russian Federation, prosp. Oktabrya, 71, Ufa, 450054

L. V. Spirikhin

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

Email: gushavaleeva@mail.ru
ORCID iD: 0000-0002-3163-882X
Russian Federation, prosp. Oktabrya, 71, Ufa, 450054

M. S. Miftakhov

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

Email: gushavaleeva@mail.ru
ORCID iD: 0000-0002-0269-7484
Russian Federation, prosp. Oktabrya, 71, Ufa, 450054

References

  1. Collins P.W., Djuric S.W. Chem. Rev. 1993, 93, 1533–1564. doi: 10.1021/cr00020a007
  2. Peng H., Chen F-E. Org. Biomol. Chem. 2017, 15, 6281–6301. doi: 10.1039/c7ob01341h
  3. Collins P.W., Djuric S.W. Chem. Rev. 2003, 93, 1534–1537. doi: 10.1021/cr00020a007
  4. Bindra J.S., Bindra R. Prostaglandin synthesis. New York: Academic Press. 1977, 187.
  5. Сапожникова Т.А., Зарудий Ф.С., Габдрахманова С.Ф., Хисамутдинова Р.Ю., Макара Н.С., Иванова Н.А., Мифтахов МС., Батталова M.О. Эксперим. и клин. фармакол. 2017, 80, 35–44. [Sapozhnikova T.A., Zarudii F.S., Gabdrakhmanova S.F., Khisamutdinova R.Yu., Makara N.S., Ivanova N.A., Miftakhov M.S., Battalova M.O. Eksperimental′naya i Klinicheskaya Farmakologiya, 2017, 80, 35–44.] doi: 10.30906/0869-2092-2017-80-8-35-44
  6. Иванова Н.А., Шайнурова А.М., Мифтахов М.С. Хим.-фарм. ж., 1998, 6, 39–40. [Ivanova N.A., Shainurova A.M., Miftakhov M.S. Pharm. Chem. J. 1998, 32, 325–326.] doi: 10.1007/BF02580520
  7. Chen S-M.L., Grudzinskas C.V., Dessy F. Prostaglandins. 1979, 17, 707–717. doi: 10.1016/s0090-6980(79)80042-8
  8. Collins P.W., Dajani E.Z., Driskill D.R., Bruhn M.S., Jung C.J., Pappo R. J. Med. Chem. 1977, 20, 1152–1159. doi: 10.1021/jm00219a008
  9. Collins P.W., Dajani E.Z., Pappo R., Gasiecki A.F., Bianchi R.G., Woods E.M. J. Med. Chem. 1983, 26, 786–790. doi: 10.1021/jm00360a002
  10. Terinek M., Kozmik V., Palecek J. Collect. Czech. Chem. Commun., 1997, 62, 1325–1341. doi: 10.1135/cccc19971325
  11. Harikrishna M., Mohan H.R., Dube P.K., Subbaraju G.V. Synth. Commun. 2009, 39, 2763–2775. doi: 10.1080/00397910802664228
  12. Иванова Н.А., Шавалеева Г.А., Мифтахов М.С. ЖОрХ. 2020, 56, 472–475. [Ivanova N.A., Shavaleeva G.A., Miftakhov M.S. Russ. J. Org. Chem. 2020, 56, 540–543.] doi: 10.1134/s1070428020030288
  13. Иванова Н.А., Шавалеева Г.А, Фазлиахметова И.Б., Мифтахов М.С. ЖОрХ. 2020, 56, 631–635. [Ivanova N.A. Shavaleeva G.A., Fazliakhmetova I.B., Miftakhov M.S. Russ. J. Org. Chem. 2020, 56, 708–711.] doi: 10.1134/s1070428020040211

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