Short total synthesis of (±)-sceptrin

被引:92
作者
Baran, PS [1 ]
Zografos, AL [1 ]
O'Malley, DP [1 ]
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
关键词
D O I
10.1021/ja049648s
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Gifted with novel chemical features and extraordinary biological activity, sceptrin has remained a prominent unanswered synthetic challenge since its characterization in 1981 by Faulkner and Clardy. A concise and practical solution to the myriad of chemical challenges posed by sceptrin is reported in this Communication. Thus, through a sequence involving rearrangement of an oxaquadricyclane, a new method for chemo- and regioselective halogenation, a mild sequence for 2-aminoimidazole formation, and careful synthetic choreography, (±)-sceptrin is obtained in a minimum of steps and in 24% overall yield from dimethyl acetylenedicarboxylate without a single use of chromatography. Copyright © 2004 American Chemical Society.
引用
收藏
页码:3726 / 3727
页数:2
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