C. Marson, Alphonso S. Rioja, K. Smith
Mar 1, 2003
Citations
0
Influential Citations
8
Citations
Journal
Synthesis
Abstract
5alpha-Androst-16-ene-3beta,5alpha-diol (12) and 5alpha-androst-16-ene-3beta,5alpha,6beta-triol (16) have been synthesised from dehydroepiandrosterone. Ketalisation and O-silylation of dehydroepiandrosterone enabled the 5alpha,6alpha-epoxide 7 to be obtained; reductive cleavage with LiAlH4 and deprotection afforded 3beta,5alpha-dihydroxy-5alpha-androstan-17-one (9) whose hydrazone was converted into the 15,16dehydro- 16-iodo sterol 11 prior to hydrodeiodination with sodium in ethanol to give 5alpha-androst-16-ene-3beta,5alpha-diol (12). Reaction of dehydroepiandrosterone with N-bromosuccinimide gave the 3beta,5alpha,6beta-ketotriol 13 which by the above three-step sequence of hydrazone formation, conversion into the vinylic iodide and reduction afforded 5alpha-androst-16-ene-3beta,5alpha,6beta-triol 16.