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

Vladimir A Khripach; Vladimir N Zhabinskii; Galina P Fando; Alla I Kuchto; Alexander S Lyakhov; Alla A Govorova; Marinus B Groen; Jaap van der Louw; Aede de Groot

doi:10.1016/j.steroids.2004.04.009

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

Steroids. 2004 Jul;69(7):495-9. doi: 10.1016/j.steroids.2004.04.009.

Authors

Vladimir A Khripach¹, Vladimir N Zhabinskii, Galina P Fando, Alla I Kuchto, Alexander S Lyakhov, Alla A Govorova, Marinus B Groen, Jaap van der Louw, Aede de Groot

Affiliation

¹ Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141 Minsk. [email protected]

PMID: 15246779
DOI: 10.1016/j.steroids.2004.04.009

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 14beta-hydroxy-17beta-tosylates, hydroboration-oxidation of the intermediate delta13(17)-olefin, and hydride reduction of the 14-ketone. An unambiguous structural assignment of (13R,14S,17S)-14,17-diacetoxy-3-methoxy-7alpha-methyl-13,14-secoestra-1,3,5(10)-triene was determined by X-ray analysis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
Models, Molecular
Molecular Conformation
Secosteroids / chemical synthesis*
X-Ray Diffraction

Substances

Secosteroids