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The estradiol derived ynone 2 is obtained via a 13 step sequence starting from estrone. One of the key-steps involves the addition to estrone derivative 3 of the lithio derivative 8. Obtention of the latter in enantiomerically pure form involves the lipase mediated kinetic resolution of racemic alcohol (±) 5. The triethylamine induced elimination of dimesylate 15 leads to the Bergman precursor...
The estradiol derived enyne 2 is obtained via a nine step sequence starting from estrone. Key-steps involve the opening of the α-epoxide 7 and the 1,2-addition of propargylmagnesium bromide on the allene ketone 10. The allylic alcohol 2 possesses the required functionalities for yielding, after dehydratation, the unsaturated core structure that is expected to cycloaromatize via Myers cyclization...
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