铜催化甾体酰基氨基乙炔的环化反应：新型11β-芳基-17,17-螺[(4'H,5'-亚甲基)恶唑]-取代甾体的合成
Copper-catalyzed cyclization of steroidal acylaminoacetylenes: syntheses of novel 11beta-aryl-17,17- spiro[(4'H,5'-methylene)oxazol]-substituted steroids.
作者信息
Jin Chunyang, Burgess Jason P, Kepler John A, Cook C Edgar
机构信息
Organic and Medicinal Chemistry, Science and Engineering Group, Research Triangle Institute, Research Triangle Park, NC 27709, USA.
出版信息
Org Lett. 2007 May 10;9(10):1887-90. doi: 10.1021/ol070447d. Epub 2007 Apr 17.
A variety of novel 11beta-aryl-17,17-spiro[(4'H,5'-methylene)oxazol]-substituted steroids have been synthesized in moderate to good yields via copper-catalyzed cyclization of acylaminoacetylenes. The best result was obtained with a catalytic amount of CuI in 1:1 benzene-Et3N at 90 degrees C for 30 min (Ar = 3,4-difluorophenyl; R = ethyl; 97% yield).
通过铜催化酰基氨基乙炔的环化反应，以中等至良好的产率合成了多种新型的11β-芳基-17,17-螺[(4'H,5'-亚甲基)恶唑]取代的甾体。在90℃下，以催化量的碘化亚铜在苯与三乙胺1:1的混合溶剂中反应30分钟，得到了最佳结果（Ar = 3,4-二氟苯基；R = 乙基；产率97%）。
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