Synthesis of oxido-bridged analogs of 18-hydroxyprogesterone.
18-Hydroxy-6,19-oxidoprogesterone and 18-hydroxy-11, 19-oxidoprogesterone were synthesized from readily available materials. The functionalization of C-18 was accomplished with phenyliodosodiacetate/iodine, whereas that of C-19 was carried out with the mercuric oxide/iodine system, both under irradiation with visible light. For 18-hydroxy-11,19-oxidoprogesterone, C-19 was functionalized before C-18, whereas the reverse order had to be used for the 6,19-oxido derivative.
Doctorovich
M O
MO
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina.
Ghini
A A
AA
Burton
G
G
D006908:Hydroxyprogesterones / Q000138:chemical synthesis* / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry; D008628:Mercury / Q000737:chemistry; D017669:Mercury Compounds; D010087:Oxides / Q000737:chemistry; D011284:Pregnenolone / Q000737:chemistry
D006908:Hydroxyprogesterones; D017669:Mercury Compounds; D010087:Oxides; C044510:18-hydroxyprogesterone; D011284:Pregnenolone; D007455:Iodine; D008628:Mercury; C019468:mercuric oxide