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Synthesis of 14,16-dien-17-yl acetates of androstane series. NMR and mass spectrometry data

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Abstract

On the basis of dehydroepiandrosterone through the Δ14- and Δ15-androst-17-ones a series of androsta-14,16-dienyl acetates was obtained, the key compounds in the synthesis of 14-substituted steroids. By the methods of two-dimensional NMR spectroscopy the structure of compounds was proved and a full assignment of signals in the 1H and 13C NMR spectra was performed. With the use of tandem mass spectrometry the main directions of fragmentation of protonated molecules of the synthesized ketones and dienyl acetates were studied.

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References

  1. Bull, J.R. and Bischofberger, K., J. Chem. Soc., Perkin Trans. 1, 1991, p. 2859.

  2. Beckmann, M., Meyer, T., Schulz, F., and Winterfeldt, E., Chem. Ber., 1994, vol. 127, p. 2505.

    Article  CAS  Google Scholar 

  3. Bull, J.R., Grundler, C., and Niven, M.L., J. Chem. Soc., Chem. Commun., 1993, p. 271.

  4. Kirsch, G., Golde, R., and Neef, G., Tetrahedron Lett., 1989, vol. 30, no. 34, p. 4497.

    Article  CAS  Google Scholar 

  5. Fell, J.D. and Heathcock, C.H., J. Org. Chem., 2002, vol. 67, no. 14, p. 4742.

    Article  CAS  Google Scholar 

  6. Baranovskii, A.V., Litvinovskaya, R.P., and Khripach, V.A., Zh. Org. Khim., 2004, vol. 40, no. 11, p. 1656.

    Google Scholar 

  7. Litvinovskaya, R.P., Baranovskii, A.V., Aver’kova, M.A., and Khripach, V.A., Bioorg. Khim., 2007, vol. 33, no. 3, p. 342.

    Google Scholar 

  8. Kelly, R.W. and Sykes, P.J., J. Chem. Soc. (C), 1968, p. 416.

  9. Cerny, I., Pouzar, V., Budesinsky, M., Drasar, P., and Havel, M., Coll. Czech. Chem. Comm., 1990, vol. 55, p. 2510.

    Article  CAS  Google Scholar 

  10. Cleve, A., Neef, G., Ottow, E., Scholz, S., and Schwede, W., Tetrahedron, 1995, vol. 51, p. 5563.

    Article  CAS  Google Scholar 

  11. Baranovskii, A.V., Litvinovskaya, R.P., Aver’kova, M.A., Khripach, N.B., and Khripach, V.A., Zh. Prikl. Spektr., 2007, vol. 74, no. 5, p. 583.

    Google Scholar 

  12. Armarego, W.L.F. and Chai, C.L.L., Purification of Laboratory Chemicals, 5th ed., Oxford: Butterworth-Heinemann, 2003.

    Google Scholar 

  13. Pataki, J. and Siade, G., J. Org. Chem., 1972, vol. 37, no. 13, p. 2127.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus’, ul. Kuprevicha 5/2, Minsk, 220141, Belarus’

    A. V. Baranovskii, D. A. Bolibrukh & V. V. Gromak

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  1. A. V. Baranovskii
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  2. D. A. Bolibrukh
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  3. V. V. Gromak
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Correspondence to A. V. Baranovskii.

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Original Russian Text © A.V. Baranovskii, D.A. Bolibrukh, V.V. Gromak, 2011, published in Zhurnal Obshchei Khimii, 2011, Vol. 81, No. 9, pp. 1540–1548.

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Baranovskii, A.V., Bolibrukh, D.A. & Gromak, V.V. Synthesis of 14,16-dien-17-yl acetates of androstane series. NMR and mass spectrometry data. Russ J Gen Chem 81, 1877 (2011). https://doi.org/10.1134/S1070363211090234

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  • DOI: https://doi.org/10.1134/S1070363211090234

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