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

作者信息

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

机构信息

Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141 Minsk.

出版信息

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

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.