Journal of the Chemical Society. Perkin transactions I p. 1269 - 1276 (1996)
Update date:2022-07-30
Topics:
Bull, James R.
Loedolff, Michiel C.
Conjugate alkylation of 3-methoxyestra-1,3,5(10),15-tetraen-17-one 1 leads to 15β-alkyl 17-ketones 2 (Me, Et or Pri), which are converted, via palladium acetate-mediated dehydrosilylation of their derived silyl enol ethers, into the corresponding 15-alkyl Δ15-17-ketones 5. Conjugate alkylation of these intermediates results in formation of 15,15-dialkyl 17-ketones 10, which undergo stereoselective reduction with lithium aluminium hydride, and deprotection of C-3 to give 15,15-dialkyl analogues 12 of estradiol. Spectroscopic data are presented to demonstrate that substrates 1 and 5 undergo exclusive 15β-alkylation.
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