The 16α-alkylation was achieved via treatment of 3-methoxyestra-1,3,5(10)-trien-17-one-N,N-dimethylhydrazone (118) with n-butyllithium and the appropriate haloalkane to afford exclusive 16α-substitution (119). Subsequent, cupric ion-catalysed hydrolysis, 17-ketone reduction and removal of the 3-hydroxyl protecting group, furnished 16α-methylestra-1,3,5(10)-trien-3,17β-diol (122a) and 16α-ethylestra-1,3,5(10)-trien-3,17β-diol (122b). An alternative sequence to the 16α-ligands, by direct alkylation of the 17-keto-estrone enolate, was also investigated. In this manner 16α-allylestra-1,3,5(10)-trien-3,17β-diol (122c) and 16α-benzylestra-1,3,5,(10)-trien-3,17β-diol (122d) were obtained.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:334350 |
| Date | January 1992 |
| Creators | Khan, Samina E. |
| Publisher | Loughborough University |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | https://dspace.lboro.ac.uk/2134/28192 |
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