The synthesis of 24-prochiral methylene steroids from nor-ketones, illustrated by the preparation of (24E)- and (24Z)-[28-2H]ergosta-5,24(28)-dien-3β-ols starting from 6β-methoxy-3α,5-cyclo-5α-cholestan-24-one (3), is described. The ketone (3) was transformed into (24E)- and (24Z)-6β-methoxy-3α,5-cyclo-5α-stigmast-24(28)-en-29-als labelled with deuterium at C-28 or at C-29 by using labelled reagents in the different steps of the reaction sequence. Stereospecific decarbonylation of the aldehyde groups then affords the prochiral methylenes.
Conversion of nor-ketones into prochiral terminal methylene groups: Synthesis of (24E)- and (24Z)-[28-2H]ergosta-5,24(28)-dien-3β- ols / M. Anastasia, P. Allevi, P. Ciuffreda, A. Fiecchi, P. Gariboldi, A. Scala. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 0(1985), pp. 595-599. [10.1039/P19850000595]
Conversion of nor-ketones into prochiral terminal methylene groups: Synthesis of (24E)- and (24Z)-[28-2H]ergosta-5,24(28)-dien-3β- ols
M. AnastasiaPrimo
;P. AlleviSecondo
;P. Ciuffreda;
1985
Abstract
The synthesis of 24-prochiral methylene steroids from nor-ketones, illustrated by the preparation of (24E)- and (24Z)-[28-2H]ergosta-5,24(28)-dien-3β-ols starting from 6β-methoxy-3α,5-cyclo-5α-cholestan-24-one (3), is described. The ketone (3) was transformed into (24E)- and (24Z)-6β-methoxy-3α,5-cyclo-5α-stigmast-24(28)-en-29-als labelled with deuterium at C-28 or at C-29 by using labelled reagents in the different steps of the reaction sequence. Stereospecific decarbonylation of the aldehyde groups then affords the prochiral methylenes.
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