Tetrahedron Letters

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

Full Text: HTML

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 ...

~90%

133152-35-9

(7α,17β)-17-[[(...

An expeditious route to 7α-substituted estradiol derivatives

[Tedesco, Rosanna; Katzenellenbogen, John A.; Napolitano, Elio Tetrahedron Letters, 1997 , vol. 38, # 46 p. 7997 - 8000]

Synthesis and testing of 17aβ-hydroxy-7α-methyl-d-homoestra-...

[Avery, Mitchell A.; Tanabe, Masato; Crowe, David F.; Detre, George; Peters, Richard H.; Chong, Wesley K. M. Steroids, 1990 , vol. 55, # 2 p. 59 - 64]

An expeditious route to 7α-substituted estradiol derivatives

[Tedesco, Rosanna; Katzenellenbogen, John A.; Napolitano, Elio Tetrahedron Letters, 1997 , vol. 38, # 46 p. 7997 - 8000]