Synthesis of Macroheterocyclic Compounds with a Furan Bridge Possessing Structural Fragments of 1,2,3-Triazoles and Natural Diterpenoids

Yuri V. Kharitonov,^a,b Makhmut M. Shakirov,^a and Elvira E. Shults^a,b@

^aNovosibirsk Institute of Organic Chemistry, 630090 Novosibirsk, Russia

^bNovosibirsk State University, 630090 Novosibirsk, Russia

^@Corresponding author E-mail: schultz@nioch.nsc.ru

DOI: 10.6060/mhc141138s
Macroheterocycles 2015 8(1) 81-88

Derivatives of natural diterpenoid lambertianic acid containing alkyne and dialkyne substituent in the furan ring were obtained. 1,2,3-Triazole-incarporated furan bridged macrocycles have been prepared by 1,3-dipolar cycloaddition of methyl 15,16-bis[(prop-2-yn-1-yloxy)methyl]lambertianate with various diazides in the presence of Cu(II)/sodium ascorbate in methylene chloride/water reaction medium.

References:

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1. Gale P.A., Gunnlaugsson T. Chem. Soc. Rev. 2010, 39, 3581-4008.
http://dx.doi.org/10.1039/c0cs90021d

2. Lee J.W., Samal S., Selvapalam N., Kim H.-J., Kim K. Acc. Chem. Res. 2003, 36, 621-630.
http://dx.doi.org/10.1021/ar020254k

3. Marsault E., Peterson M.L. J. Med. Chem. 2011, 54, 1961-2004.
http://dx.doi.org/10.1021/jm1012374

4. Virtanen E., Kolehmainen E. Eur. J. Org. Chem. 2004, 3385-3399.
http://dx.doi.org/10.1002/ejoc.200300699

5. Cho H., Widanapathirana L., Zhao Y. J. Am. Chem. Soc. 2011, 133, 141-147.
http://dx.doi.org/10.1021/ja109036z

6. Bag B.G., Dinda S.K., Dey P.P., Mallia V.A., Weiss R.G. Langmuir 2009, 25, 8663-8671.
http://dx.doi.org/10.1021/la8042796

7. Hu J., Li R., Lu J., Ju Y. Tetrahedron Lett. 2011, 52, 4211-4214.
http://dx.doi.org/10.1016/j.tetlet.2011.06.022

8. Hu J., Wu J., Lu J., Ju Y. Tetrahedron Lett. 2012, 53, 6705-6709.
http://dx.doi.org/10.1016/j.tetlet.2012.09.118

9. Chattopadhyay P., Pandey P.S. Tetrahedron 2006, 62, 8620-8624.
http://dx.doi.org/10.1016/j.tet.2006.06.029

10. Juráŝek M., Džubák P., Sedlák D., Dvořáková H., Hajdúch M., Bartunĕk P., Drašar P. Steroids 2013, 78, 356-361.
http://dx.doi.org/10.1016/j.steroids.2012.11.016

11. Hu J., Zhang M., Yu L. B., Ju Y. Bioorg. Med. Chem. Lett., 2010, 20, 4342-4346.
http://dx.doi.org/10.1016/j.bmcl.2010.06.079

12. Kataev V.E., Khaybullin R.N., Sharipova R.R., Strobykina I.Yu. Rev. J. Chem. 2011, 1, 93-160.
http://dx.doi.org/10.1134/S2079978011010043

13. Andreeva O.A., Strobykina I.Yu., Kataeva O.N., Dobrynin A.B., Babaev V.M., Rizvanov I.Kh., Islamov D.R., Kataev V.E. Macroheterocycles 2013, 6, 315-322.
http://dx.doi.org/10.6060/mhc131056k

14. Khaybullin R.N., Strobykina I.Yu., Dobrynin A.B., Gubaydullin A.T., Chestnova R.V., Babaev V.M., Kataev V.E. Bioorg. Med. Chem. Lett. 2012, 22, 6909-6913.
http://dx.doi.org/10.1016/j.bmcl.2012.09.023

15. Ojima I., Das M. J. Nat. Prod. 2009, 72, 554-565.
http://dx.doi.org/10.1021/np8006556

16. Meldal M., Tornoe C.W. Chem. Rev. 2008, 108, 2952-3015.
http://dx.doi.org/10.1021/cr0783479

17. Kharitonov Yu.V., Shul'ts E.E., Shakirov M.M., Bagryanskaya I.Yu., Tolstikov G.A. Doklady Chemistry, 2012, 446, 174-179.
http://dx.doi.org/10.1134/S0012500812090042

18. Blunt J.W., Copp B.R., Keyzers R.A., Munro M.H.G., Prinsep M.R. Nat. Prod. Rep. 2013, 30, 237-323.
http://dx.doi.org/10.1039/C2NP20112G

19. Patent RF 2460741 Invention Bull. 2012, N 9 (in Russ.).

20. Klok D.A., Shakirov M.M., Grishko V.V., Raldugin V.A. Russ. Chem. Bull. (Engl. Transl.) 1995, 44, 2412-2414 [Izv. Akad. Nauk, Ser. Khim. 1995, 2514-2517 (in Russ.)].

21. Saikia B., Saikia P.P., Goswami A., Barua N.C., Saxena A.K., Suri N. Synthesis 2011, 3173-3179.

22. Katrytzky A.R, Meher N.K., Hanci S., Gyanda R., Tala S.R., Mathai S., Duran R.S., Bernard S., Sabri F., Singh S.K., Doskocz J., Ciaramitaro D.A. J. Polymer Sci. A, Pol. Chem. 2008, 46, 238-256.
http://dx.doi.org/10.1002/pola.22376

23. Klein E., DeBonis S., Thiede B., Skoufias D.A., Kozielski F., Lebeau L. Bioorg. Med. Chem. 2007, 15, 6474-6488.
http://dx.doi.org/10.1016/j.bmc.2007.06.016

24. Kharitonov Yu.V.,Shul’ts E.E.,Shakirov M.M.,Pokrovsky М.A.,Pokrovsky A.G.,Tolstikov G.A. Russ.Chem.Bull. 2013, 62, 2046-2055.
http://dx.doi.org/10.1007/s11172-013-0297-5

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Synthesis of Macroheterocyclic Compounds with a Furan Bridge Possessing Structural Fragments of 1,2,3-Triazoles and Natural Diterpenoids

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