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…]
A Masters Thesis. Submitted in partial fulfilment of the requirements for the award of Master of Philosophy of Loughborough University.
National Council of Research and Technology (CONACYT), Mexico.