Stereocontrolled derivatization of 3-methoxyestra-1,3,5(10), n-tetraenes via lewis acid promoted prins reactions, (n=7; 8(9))

Add time:08/04/2019    Source:sciencedirect.com

Steroidal olefins 1 and 3 undergo dimethylaluminum chloride-mediated Prins reactions with paraformaldehyde to furnish homoallylic alcohols 4 and 16 as major products. These ene reaction-type intermediates are converted into 6 and 17 by hydroxyl group-assisted catalytic hydrogenation, while Birch reduction of 4 proceeds to the 8β-epimer 11. The saturated alcohols thus obtained serve as convenient precursors to methyl derivatives 10, 14, and 20.

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