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

Authors :: Khripach, Vladimir A.
Zhabinskii, Vladimir N.
Fando, Galina P.
Kuchto, Alla I.
Lyakhov, Alexander S.
Govorova, Alla A.
Groen, Marinus B.
van der Louw, Jaap
de Groot, Aede
Source :: Steroids. Jul2004, Vol. 69 Issue 7, p495-499. 5p.
Publication Year :: 2004
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 14β-hydroxy-17β-tosylates, hydroboration–oxidation of the intermediate Δ13(17)-olefin, and hydride reduction of the 14-ketone. An unambiguous structural assignment of (13R,14S,17S)-14,17-diacetoxy-3-methoxy-7α-methyl-13,14-secoestra-1,3,5(10)-triene was determined by X-ray analysis. [Copyright &y& Elsevier]