Stereocontrolled derivatization of 3-methoxyestra-1, 3, 5 (10), n-tetraenes via lewis acid promoted prins reactions,(n= 7; 8 (9))
H Künzer, G Sauer, R Wiechert
Index: Kuenzer, Hermann; Sauer, Gerhard; Wiechert, Rudolf Tetrahedron Letters, 1991 , vol. 32, # 6 p. 743 - 746
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Citation Number: 9
Abstract
Abstract 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 ...
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