Tetrahedron letters

A new, stereoselective approach to C (7)-alkylated estra-1, 3, 5 (10)-triene derivatives

H Künzer, M Thiel, G Sauer, R Wiechert

Index: Kuenzer, H.; Thiel, M.; Sauer, G.; Wiechert, R. Tetrahedron Letters, 1994 , vol. 35, # 11 p. 1691 - 1694

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Citation Number: 13

Abstract

Abstract 17β-Acetyloxy-3-methoxy-6-(phenylsulfonyl) estra-1, 3, 5 (10), 6-tetraene (4) was prepared as a substrate for conjugate addition of organolithium reagents by a three-step sequence starting from 17β-acetyloxy-3-methoxyestra-1, 3, 5 (10)-trien-6-one (2). While methyllithium showed only poor face selectivity, higher alkyllithium species (n-BuLi, t-BuLi) preferred to add to the β-face of 4. 7α-Substituted derivatives, on the other hand, were ...

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