The synthesis of functionalized 13,14-seco-steroids via Grob fragmentation

V.A. Khripach, V.N. Zhabinskii, G.P. Fando, A.I. Kuchto, A.S. Lyakhov, A.A. Govorova, M.B. Groen, J. van der Louw, Æ. de Groot

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13 Citations (Scopus)

Abstract

A synthetic methodology for the synthesis of 13,14-seco-steroids with substituents at C-14 and C-17 is described. The approach involves Grob fragmentation of 14ß-hydroxy-17ß-tosylates, hydroboration–oxidation of the intermediate ¿13(17)-olefin, and hydride reduction of the 14-ketone. An unambiguous structural assignment of (13R,14S,17S)-14,17-diacetoxy-3-methoxy-7a-methyl-13,14-secoestra-1,3,5(10)-triene was determined by X-ray analysis.
Original languageEnglish
Pages (from-to)495-499
JournalSteroids
Volume69
Issue number7
DOIs
Publication statusPublished - 2004

Keywords

  • heterolytic fragmentation
  • steroids

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    Khripach, V. A., Zhabinskii, V. N., Fando, G. P., Kuchto, A. I., Lyakhov, A. S., Govorova, A. A., Groen, M. B., van der Louw, J., & de Groot, Æ. (2004). The synthesis of functionalized 13,14-seco-steroids via Grob fragmentation. Steroids, 69(7), 495-499. https://doi.org/10.1016/j.steroids.2004.04.009