A study to develop novel lipophilic metal ion complexes based on
dihydrocholesterol was undertaken.
Steroid ligands functionalised at the 2- and 3- positions were
synthesized as possible bidentate ligands for complexation of metal
ions. Condensation of 5α-cholestan-3-one with ethyl formate in the
presence of base gave 2-hydroxymethylene-5α-cholestan-3-one, and 2-
acetyl-5α-cholestan-3-one was obtained by the reaction between 3-
trimethylsilyloxy-5α-cholest-2-ene and acetyl chloride. Attempts to
synthesize 2,3-dioximino-5α-cholestane from 5α-cholestan-3-one and
2α-hydroxy-5α-cholestan-3-one were unsuccessful. Likewise 2-
methylene-5α-cholestan-3-one, which was expected to lead to other
bidentate ligands, could not be prepared satisfactorily from 5α-cholestan-
3-one or 3-trimethylsilyloxy-5α-cholest-2-ene. [Continues.]
A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy at Loughborough University.