A versatile synthesis of 17-heteroaryl androstenes via palladium-mediated Suzuki cross-coupling with heteroaryl boronic acids.
Suzuki coupling of 17-iodoandrosta-5,16-dien-3beta-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(PPh(3))(4), 2M Na(2)CO(3) and MeOH), generally yielded C(17)-heteroaryl steroids in moderate (10-60%) yields, but furanyl-2- and 5-chlorothienyl-2-boronic acid did not give any coupling product.
Chao
Jianping
J
School of Materials and Chemical Engineering, Beijing Institute of Petrochemical Technology, Beijing 102600, China.
Ling
Yangzhi
Y
Liu
Xiaofeng
X
Luo
Xuande
X
Brodie
A M H
AM
D000736:Androstenes / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D065607:Cytochrome P-450 Enzyme Inhibitors; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*
D000736:Androstenes; D001897:Boronic Acids; D065607:Cytochrome P-450 Enzyme Inhibitors; D004791:Enzyme Inhibitors; D010165:Palladium; D003577:Cytochrome P-450 Enzyme System