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Number of results

Journal

2013 | 11 | 12 | 2144-2150

Article title

Stereoselective preparation of mono- and bis-derivatives of pentacyclo[6.3.0.02,6.03,10.05,9] undecane (D
3-trishomocubane)

Content

Title variants

Languages of publication

EN

Abstracts

EN
The rearrangement of easily accessible Cookson’s diketone with chlorosulfonic acid in chloroform followed by the acidic hydrolysis gave 6-chloro-7-hydroxy-dichloropentacyclo[6.3.0.02,6.03,10.05,9]undecane-4-one, whose syn-stereochemistry was assigned through the X-ray crystal structure analysis. This key structure was used for the stereoselective synthesis of the D 3-trishomocubane derivatives as well as for the preparation of potential drugs bearing hydroxy- and amino-functional groups. A new multigram preparative synthesis of D 3-trishomocubane was developed. [...]

Publisher

Journal

Year

Volume

11

Issue

12

Pages

2144-2150

Physical description

Dates

published
1 - 12 - 2013
online
26 - 9 - 2013

Contributors

  • Department of Organic Chemistry, Kiev Polytechnic Institute, 03056, Kiev, Ukraine
  • Department of Organic Chemistry, Kiev Polytechnic Institute, 03056, Kiev, Ukraine
  • Department of Organic Chemistry, Kiev Polytechnic Institute, 03056, Kiev, Ukraine
  • Department of Organic Chemistry, Kiev Polytechnic Institute, 03056, Kiev, Ukraine
  • Institute of Organic Chemistry, Justus-Liebig University, D-35392, Giessen, Germany
author
  • Department of Organic Chemistry, Kiev Polytechnic Institute, 03056, Kiev, Ukraine
  • Department of Organic Chemistry, Kiev Polytechnic Institute, 03056, Kiev, Ukraine

References

  • [1] G.R. Underwood, B. Ramamoorthy, Tetrahedron Lett. 11, 4125 (1970) http://dx.doi.org/10.1016/S0040-4039(01)98683-6[Crossref]
  • [2] D.M. Ho, R.A. Pascal, Chem. Mater. 5, 1358 (1993) http://dx.doi.org/10.1021/cm00033a029[Crossref]
  • [3] A.V. Gaidai, D.M. Volochnyuk, O.V. Shishkin, A.A. Fokin, I.A. Levandovskiy, T.E. Shubina, Synthesis 810 (2012)
  • [4] A. Sklyarova, V. Rodionov, C. Parsons, G. Quack, P. Schreiner, A. Fokin, Med. Chem. Res. 360 (2012)
  • [5] G.J. Kent, S.A. Godleski, E. Osawa, P.v.R. Schleyer, J. Org. Chem. 42, 3852 (1977) http://dx.doi.org/10.1021/jo00444a012[Crossref]
  • [6] S.A. Godleski, P.v.R. Schleyer, E. Osawa, G.J. Kent, J. Chem. Soc., Chem. Commun. 976 (1974) [Crossref]
  • [7] K. Naemura, T. Fujii, H. Chikamatsu, Chem. Lett. 15, 923 (1986) http://dx.doi.org/10.1246/cl.1986.923[Crossref]
  • [8] D.W. Oliver, T.G. Dekker, S. Afr. J. Chem. 32, 45 (1979)
  • [9] M. Nakazaki, K. Naemura, N. Arashiba, J. Org. Chem. 43, 689 (1978) http://dx.doi.org/10.1021/jo00398a038[Crossref]
  • [10] P.E. Eaton, B. Leipzig, J. Org. Chem. 43, 2483 (1978) http://dx.doi.org/10.1021/jo00406a042[Crossref]
  • [11] M. Nakazaki, H. Chikamatsu, K. Naemura, T. Suzuki, M. Iwasaki, Y. Sasaki, T. Fujii, J. Org. Chem. 46, 2726 (1981) http://dx.doi.org/10.1021/jo00326a025[Crossref]
  • [12] R. C. Cookson, E. Crundwell, R.R. Hill, J. Hudec, J. Chem. Soc. 3062 (1964) [Crossref]
  • [13] G.A. Tolstikov, B.M. Lerman, F.Z. Galin, Zh. Org. Khim. 12, 1133 (1976)
  • [14] D.I. Sharapa, A.V. Gayday, A.G. Mitlenko, I.A. Levandovskiy, T.E. Shubina, Eur. J. Org. Chem. 2011, 2554 (2011) http://dx.doi.org/10.1002/ejoc.201001731
  • [15] G. Helmchen, G. Staiger, Angew. Chem. Int. Ed. 16, 116 (1977) http://dx.doi.org/10.1002/anie.197701161[Crossref]
  • [16] G.A. Tolstikov, B.M. Lerman, F.Z. Galin, Y.T. Struchkov, V.G. Andrianov, Tetrahedron Lett. 19, 4145 (1978) http://dx.doi.org/10.1016/S0040-4039(01)95166-4[Crossref]
  • [17] D.W. Oliver, T.G. Dekker, F.O. Snyckers, T.G. Fourie, J. Med. Chem. 34, 851 (1991) http://dx.doi.org/10.1021/jm00106a053[Crossref]
  • [18] A.J.M. Carpy, D.W. Oliver, Helv. Chim. Acta 77, 543 (1994) http://dx.doi.org/10.1002/hlca.19940770215[Crossref]
  • [19] C. Zlotogorski, J. Blum, E. Osawa, H. Schwarz, G. Hoehne, J. Org. Chem. 49, 971 (1984). http://dx.doi.org/10.1021/jo00180a004[Crossref]
  • [20] V.T. Nguyen, P.D. Ahn, R. Bishop, M.L. Scudder, D.C. Craig, Eur. J. Org. Chem. 4489 (2001) [Crossref]
  • [21] C.J. Van der Schyf, W.J. Geldenhuys, Neurotherapeutics 6, 175 (2009) http://dx.doi.org/10.1016/j.nurt.2008.10.037[Crossref]
  • [22] W.J. Geldenhuys, S.F. Mala, J.R. Bloomquist, A.P. Marchand, C.J.V.d. Schyf, Med. Res. Rev. 25, 21 (2005) http://dx.doi.org/10.1002/med.20013[Crossref]
  • [23] G.M. Sheldrick, Programs for the Solution of Crystal Structures, SHELXS97 and SHELXL97 (University of Gottingen, Germany, 1997)
  • [24] G. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr. 64, 112 (2008) http://dx.doi.org/10.1107/S0108767307043930[Crossref]
  • [25] G. Mehta, A.V. Reddy, A. Srikrishna, J. Chem. Soc., Perkin Trans. 291 (1986) [Crossref]
  • [26] E.C. Smith, J.C. Barborak, J. Org. Chem. 41, 1433 (1976) http://dx.doi.org/10.1021/jo00870a032[Crossref]

Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.-psjd-doi-10_2478_s11532-013-0339-8
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