A versatile synthesis of 17-heteroaryl androstenes via palladium-mediated Suzuki cross-coupling with heteroaryl boronic acids

J Chao, Y Ling, X Liu, X Luo, AMH Brodie

Index: Chao, Jianping; Ling, Yangzhi; Liu, Xiaofeng; Luo, Xuande; Brodie Steroids, 2006 , vol. 71, # 7 p. 585 - 590

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Citation Number: 15

Abstract

Suzuki coupling of 17-iodoandrosta-5, 16-dien-3β-ol (1) and 17-iodoandrosta-4, 16-dien-3- one (2) with nine heteroaryl boronic acids (mainly 2-or 3-furanyl, thienyl, benzofuranyl and benzothienyl boronic acid derivatives) were carried out under normal Suzuki condition (Pd (PPh3) 4, 2M Na2CO3 and MeOH), generally yielded C17-heteroaryl steroids in moderate (10–60%) yields, but furanyl-2-and 5-chlorothienyl-2-boronic acid did not give any ...