Synthesis of nitrogen- and oxygen-containing macrocycles--derivatives of lithocholic Acid.
Palladium-catalyzed amination of 3,24-bis(3-bromophenoxy)cholane (4) with various polyamines and polyoxadiamines 5 taken in 1:1 ratio was used for the synthesis of the macrocycles 6, which contain steroidal and polyamine moieties and were obtained in 38-65 % yields. The same reaction with excess polyamine (2.2-3 equiv) provided bis(polyamino) derivatives of 3,24-diphenoxycholane 7 in excellent yields, whereas the diarylation of polyamines with two equivalents of 3,24-bis(3-bromophenoxy)cholane afforded their bis(steroidal) derivatives 8. Compounds 7 and 8 were employed in the syntheses of cyclodimers 9, which possess two steroidal and two polyamine fragments; the efficiency of two methods was compared.
Averin
Alexei D
AD
Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, Moscow, Russia.
Ranyuk
Elena R
ER
Lukashev
Nikolai V
NV
Beletskaya
Irina P
IP
D008095:Lithocholic Acid / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D009584:Nitrogen / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D008095:Lithocholic Acid; D009584:Nitrogen; D010100:Oxygen