Tetrahedron Letters

Protecting group effect on the 1, 2-dehydrogenation of 19-hydroxysteroids: a highly efficient protocol for the synthesis of estrogens

Y Jing, CG Xu, K Ding, JR Lin, RH Jin, WS Tian

Index: Jing, Yu; Xu, Cheng-Gong; Ding, Kai; Lin, Jing-Rong; Jin, Rong-Hua; Tian, Wei-Sheng Tetrahedron Letters, 2010 , vol. 51, # 24 p. 3242 - 3245

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Citation Number: 8

Abstract

19-O-Acylation was found to be indispensable for 1, 2-dehydrogenation of 19- hydroxyandrost-4-ene-3, 17-dione 1a with DDQ as an oxidant after exploring a variety of C- 19 substituents. 1, 2-Dehydrogenation in combination with subsequent A-ring aromatization via retro-aldol reaction provided a flexible and efficient protocol for the synthesis of estrogens. To demonstrate the utility of the protocol, pharmaceutically attractive estrogens ...