TY - JOUR
T1 - Synthesis of 11‐Oxaestrogens via Dye‐Sensitized Photo‐oxygenation of a 9,11‐Didehydroestrone Derivative
AU - Planas, Antoni
AU - Sala, Nuria
AU - Bonet, Juan‐Julio ‐J
PY - 1989/6/14
Y1 - 1989/6/14
N2 - The 3‐methoxy‐1 1‐oxaestrone (13) has been synthetized from estrone (3) following an approach that involves the ring‐C fragmentation of the estrogenic skeleton by dye‐sensitized photo‐oxygenation of the properly C(17)‐protected 9,11‐didehydroestrone derivative 6 as the key step. The C(13)‐side‐chain degradation of the 9‐oxo‐9,11‐seco‐aldehyde 7 followed by reduction to the 9β, 12‐diol 10 and further cyclization yields the 11‐oxaestrogenic skeleton. By this procedure, 13 is obtained in 9 steps from 3 with a non‐optimized overall yield of ca. 15%.
AB - The 3‐methoxy‐1 1‐oxaestrone (13) has been synthetized from estrone (3) following an approach that involves the ring‐C fragmentation of the estrogenic skeleton by dye‐sensitized photo‐oxygenation of the properly C(17)‐protected 9,11‐didehydroestrone derivative 6 as the key step. The C(13)‐side‐chain degradation of the 9‐oxo‐9,11‐seco‐aldehyde 7 followed by reduction to the 9β, 12‐diol 10 and further cyclization yields the 11‐oxaestrogenic skeleton. By this procedure, 13 is obtained in 9 steps from 3 with a non‐optimized overall yield of ca. 15%.
UR - http://www.scopus.com/inward/record.url?scp=0024402631&partnerID=8YFLogxK
U2 - 10.1002/hlca.19890720412
DO - 10.1002/hlca.19890720412
M3 - Article
AN - SCOPUS:0024402631
SN - 0018-019X
VL - 72
SP - 725
EP - 730
JO - Helvetica Chimica Acta
JF - Helvetica Chimica Acta
IS - 4
ER -