The synthesis of functionalized 13,14-seco-steroids via Grob fragmentation.
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.
Khripach
Vladimir A
VA
Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141 Minsk. khripach@iboch.bas-net.by
Zhabinskii
Vladimir N
VN
Fando
Galina P
GP
Kuchto
Alla I
AI
Lyakhov
Alexander S
AS
Govorova
Alla A
AA
Groen
Marinus B
MB
van der Louw
Jaap
J
de Groot
Aede
A
D003500:Cyclization; D008958:Models, Molecular; D008968:Molecular Conformation; D012632:Secosteroids / Q000138:chemical synthesis*; D014961:X-Ray Diffraction
D012632:Secosteroids