Aspects of steroidal partial synthesis and rearrangements
thesisposted on 2017-08-24, 13:36 authored by Rafael T. Silva
The previously reported conversion of 3ß-tosyloxy-5α-cholestane-5, 6ß-diol with Buᵗ0K/Buᵗ0H to 3ß-methyl-A-nor-5ß-cholestan-5-ol-6-one, is believed to arise from a novel intramolecular ene reaction of an intermediate unsaturated acyloin, 4,5-seco-cholest-3-en-6ß-ol-5-one. It was proposed to synthesise the unsaturated acyloin 4,5-secocholest- 3-en-6ß-ol-5-one to determine whether it would indeed undergo the ene reaction. [continues…]
National Council of Research and Technology (CONACYT), Mexico.