Nitrogen-containing tricyclic and tetracyclic compounds by stereoselective samarium diiodide promoted cyclizations of quinolyl-substituted ketones -: A new access to azasteroids

被引:24
作者
Aulenta, Francesca [1 ,2 ]
Wefelscheid, Ulrike K. [1 ]
Bruedgam, Irene [1 ]
Reissig, Hans-Ulrich [1 ]
机构
[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany
[2] BASF GKT W B 001, Polymer Res Biopolymers, D-67056 Ludwigshafen, Germany
关键词
samarium; electron transfer; quinolines; steroids; C-Ccoupling;
D O I
10.1002/ejoc.200800019
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this report, we describe our experiments dealing with samarium diiodide promoted cyclizations of quinolyl-substituted ketones 6 - 12 and also the attempted reductive cyclization of carbazole-containing ketone 13. These precursors were prepared by Heck-type coupling reactions of the corresponding hetaryl nonaflates with adequately substituted olefins as a key step. The cyclization of compounds 7 - 12 led to nitrogen-containing tri- and tetracyclic compounds 23 - 28 in moderate to good yields and generally proceeded in a highly diastereoselective fashion. The azatetracycles present steroid-like skeletons but with unnatural cis - cis annulation of rings B, C and D. We also describe the chemical modification of the styrene-type double bond of these products, which provided highly functionalized steroid-type compounds such as 29, 30 and 32. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
引用
收藏
页码:2325 / 2335
页数:11
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