The First Example of Cascade Synthesis of Alkaloid-like Subunit Incorporated into Crown Ethers

Irina G. Ovchinnikova,^@1 Olga V. Fedorova, Eugenia G. Matochkina, Mikhail I. Kodess, Andrey A. Tumashov, Pavel A. Slepukhin, Gennady L. Rusinov, and Valery N. Charushin^@2

I.Y. Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Science, 620041 Ekaterinburg, GSP-147, Russia

^@1Corresponding author E-mail: iov@ios.uran.ru

^@2Corresponding author E-mail: charushin@ios.uran.ru

DOI: 10.6060/mhc2010.2-3.108

A new type of template-assisted cyclization was found to occur in the course of nucleophilic reactions on chalcone podands, thus resulting in the formation of rather new complex polycyclic compounds. The structure of 25-methyl-
23,29-diphenyl-8,11,14-trioxa-24-azahexa-cyclo[20.8.0.02,7.015,20.021,26.025,30]triaconta-2,4,6,15(20),16,18,23,28-octaene-27-one was established by means of IR (DRA), 1H and 13С NMR spectroscopy, as well as the X-ray crystallography. Polycyclic crownophane with the core of 2-azabicyclo[2.2.2]oct-2-ene can be regarded as synthetic analogues of Daphniphyllum alkaloids.

Keywords: Template synthesis, chalcone podands, crown ethers, alkaloids, cascade reactions.

References:

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1. Litvinov V.P. Russ. Chem. Rev. 2003, 72 (1), 69 – 85.
http://dx.doi.org/10.1070/RC2003v072n01ABEH000764

2. a) Bienayme H., Hulme C., Oddon G., Schmitt P. Chem. Eur. J. 2000, 6(18), 3321 – 3329;
http://dx.doi.org/10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO;2-A
b) Nefzi A., Ostresh J.M., Houghten R.A. Chem. Rev. 1997, 97, 449 – 472.
http://dx.doi.org/10.1021/cr960010b

3. a) Kappe C.O. Acc. Chem. Rec. 2000, 33, 879 – 888;
http://dx.doi.org/10.1021/ar000048h
b) Evdokimov N.M., Kireev A.S., Yakovenko A.A., Antipin M.Y., Magedov I.V., Kornienko A. J. Org. Chem. 2007, 72, 3443 – 3457;
http://dx.doi.org/10.1021/jo070114u
c) Smith C.D., Gavrilyuk J.I., Lough A.J., Batey R.A. J. Org. Chem. 2010, 75, 702 – 715;
http://dx.doi.org/10.1021/jo9021106
d) Jiang B., Li C., Shi F., Tu S., Kaur P., Wever W., Li G. J. Org. Chem. 2010, 75, 2962 – 2965.
http://dx.doi.org/10.1021/jo1002278

4. Tietze L.F. Chem. Rev. 1996, 96, 115 – 136.
http://dx.doi.org/10.1021/cr950027e

5. Parsons P.J., Penkett C.S., Shell A.J. Chem. Rev. 1996, 96, 195 – 206.
http://dx.doi.org/10.1021/cr950023+

6. Gaich T., Baran P.S. J. Org. Chem. 2010, 75, 4657 – 4673.
http://dx.doi.org/10.1021/jo1006812

7. a) Burke S.D., Murtiashaw C.W., Saunders J.O., Oplinger J.A., Dike M.S. J. Am. Chem. Soc. 1984, 106, 4558 – 4566;
http://dx.doi.org/10.1021/ja00328a043
b) Danishefsky S., Vaughan K., Gadwood R., Tsuzuki K. J. Am. Chem. Soc. 1981, 103, 4136 – 4141;
http://dx.doi.org/10.1021/ja00404a026
c) Bornack W. K., Bhagwat S.S., Ponton J., Helquist P. J. Am. Chem. Soc. 1981, 103, 4647 – 4648.
http://dx.doi.org/10.1021/ja00405a091

8. a) Suzuki M., Yanagisawa A., Noyori R. J. Am. Chem. Soc. 1988, 110, 4718 – 4726;
http://dx.doi.org/10.1021/ja00222a033
b) Johnson C.R., Penning T.D. J. Am. Chem. Soc. 1988, 110, 4726 – 4735;
http://dx.doi.org/10.1021/ja00222a034
c) Lipshutz B.H., Wood M.R. J. Am. Chem. Soc. 1994, 116, 11689 – 11702.
http://dx.doi.org/10.1021/ja00105a010

9. a) Ruggeri R.B., Hansen M.M., Heathcock C.H. J. Am. Chem. Soc. 1988, 110, 8734 – 8736;
http://dx.doi.org/10.1021/ja00234a046
b) Wallace G.A., Heathcock C.H. J. Org. Chem. 2001, 66, 450 – 454;
http://dx.doi.org/10.1021/jo001145r
c) Bitar H.E., Nguyen V.H., Gramain A., Sévenet T., Bodo B. Tetrahedron Lett. 2004, 45, 515–518;
http://dx.doi.org/10.1016/j.tetlet.2003.11.005
d) Kobayashi J., Kubota T. Nat. Prod. Rep. 2009, 26, 936 – 962.
http://dx.doi.org/10.1039/b813006j

10. a) Martin S.F., Desai S.R., Phillips G.W., Miller A.C. J. Am. Chem. Soc. 1980, 102, 3294 – 3296;
http://dx.doi.org/10.1021/ja00529a089
b) Funk R.L., Vollhardt K.P.C. J. Am. Chem. Soc. 1980, 102, 5253 – 5261;
http://dx.doi.org/10.1021/ja00536a023
c) Stork G., Chan T.Y. J. Am. Chem. Soc. 1995, 117, 6595 – 6596;
http://dx.doi.org/10.1021/ja00129a025
d) Shing T.K.M., Yang J. J. Org. Chem. 1995, 60, 5785 – 5789;
http://dx.doi.org/10.1021/jo00123a011
e) Roush W.R., Koyama K., Curtin M.L., Moriarty K.J. J. Am. Chem. Soc. 1996, 118, 7502 – 7512;
http://dx.doi.org/10.1021/ja9607796
f) Winkler J.D., Kim H.S., Kim S., Ando K., Houk K.N. J. Org. Chem. 1997, 62, 2957 – 2962;
http://dx.doi.org/10.1021/jo961620e
g) Batey R.A., Thadani A.N., Lough A.J. J. Am. Chem. Soc. 1999, 121, 450 – 451;
http://dx.doi.org/10.1021/ja9828004
h) Toró A., Nowak P., Deslongchamps P. J. Am. Chem. Soc. 2000, 122, 4526 – 4527;
http://dx.doi.org/10.1021/ja000728f
i) Waizumi N., Itoh T., Fukuyama T. J. Am. Chem. Soc. 2000, 122, 7825 – 7826;
http://dx.doi.org/10.1021/ja001664b
j) Wada E., Kumaran G., Kanemasa S. Tetrahedron Lett. 2000, 41, 73 – 76.
http://dx.doi.org/10.1016/S0040-4039(99)02003-1

11. a) Host Guest Complex Chemistry Macrocycles. Synthesis, Structures, Applications (F. Vögtle, E. Weber, Eds) Springer-Verlag, Berlin, 1985;
b) Gokel G.W. Crown Ethers and Cryptands (Monographs in Supramolecular Chemistry) The Royal Society of Chemistry: Cambridge, 1991, 3, 190;
c) Fenlon E.E. Eur. J. Org. Chem. 2008, 5023 – 5035.
http://dx.doi.org/10.1002/ejoc.200800578

12. Weber E., Toner J.L., Goldberg I., Vögtle F., Laidler D.A., Stoddart J.F., Bartsch R.A., Liotta C.L. Crown Ethers and Analogs John Wiley & Sons: Chichester, 1989, 558.
http://dx.doi.org/10.1002/9780470772232

13. Ovchinnikova I.G., Fedorova O.V., Matochkina E.G., Kodess M.I., Slepukhin P.A., Rusinov G.L. Russ. Chem. Bull.,Int. Ed. 2009, 58(6), 1180 – 1191.
http://dx.doi.org/10.1007/s11172-009-0154-8

14. OvchinnikovaI.G., FedorovaO.V., SlepukhinP.A., LitvinovI.A., RusinovG.L. Crystallogr. Rep. 2009, 54(1), 31 – 39.
http://dx.doi.org/10.1134/S1063774509010064

15. a) Arrowsmith J., Jennings Sh.A., Langnel D.A.F., Wheelhouse R.T., Stevens M.F.G. J. Chem. Soc. Perkin Trans. 1 2000, 24, 4432 – 4438;
http://dx.doi.org/10.1039/b005652i
b) Molina P., Tarraga A., Diaz I., Espinosa A., Gaspar C. Heterocycles 1993, 36, 1263 – 1278;
http://dx.doi.org/10.3987/COM-92-6275
c) Katritzky A.R., Belyakov S.A., Denisko O.V., Maran U., Dalal N.S. J. Chem. Soc., Perkin Trans. 2 1998, N. 3, 611 – 616;
http://dx.doi.org/10.1039/a707561h
d) Yildiz M., Kilic Z., Hokelek T. J. Molecular Structure 1999, 510, 227 – 235.
http://dx.doi.org/10.1016/S0022-2860(99)00098-8

16. a) Van Bergen T.J., Kellogg R.M. J. Chem. Soc., Chem. Commun. 1976, 964 – 965;
http://dx.doi.org/10.1039/c39760000964
b) Zhidovinova M.S., Fedorova O.V., Rusinov G.L., Ovchinnikova I.G. Molecular Diversity 2003, 6, 323 – 326;
http://dx.doi.org/10.1023/B:MODI.0000006915.32225.3a
c) Levov A.N., Le Tuan Anh, Komarova A.I., Strokina V.M., Soldatenkov A.T., Khrustalev V.N. Russ. J. Org. Chem. 2008, 44(3), 456 – 461;
http://dx.doi.org/10.1134/S1070428008030238
d) Le Tuan Anh, Levov A.N., Soldatenkov A.T., Gruzdev P.D., Chyong Khong Khieu Russ. J. Org. Chem. 2008, 44(3), 462 – 464.

17. Cram D.J. Angew. Chem., Int. Ed. Engl. 1986, 25, 1039 – 1057.
http://dx.doi.org/10.1002/anie.198610393

18. Sheldrick G.M. ActaCrystallogr., Sect. A: Found. Crystallogr. 2008, 64, 112.
http://dx.doi.org/10.1107/S0108767307043930

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