Synthesis of 11-Oxaestrogens via Dye-Sensitized Photo-oxygenation of a 9,11-Didehydroestrone Derivative

@inproceedings{Planas1989SynthesisO1,
  title={Synthesis of 11-Oxaestrogens via Dye-Sensitized Photo-oxygenation of a 9,11-Didehydroestrone Derivative},
  author={Antoni Planas and N{\'u}ria Menta Sala and J. J. Bonet},
  year={1989}
}
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… CONTINUE READING