Total synthesis of mucocin

被引:57
作者
Neogi, P
Doundoulakis, T
Yazbak, A
Sinha, SC
Sinha, SC
Keinan, E
机构
[1] Scripps Res Inst, Dept Biol Mol, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[3] Technion Israel Inst Technol, Dept Chem, IL-32000 Haifa, Israel
关键词
D O I
10.1021/ja981302s
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis of the potent antitumor agent, mucocin, 1, was efficiently achieved in 20 steps from cyclododecatriene, thus confirming the proposed structure of this unusual member of the Annonaceous acetogenins. Demonstrating the power of the "naked" carbon skeleton strategy, all seven asymmetric centers in the key fragment of the molecule were introduced by double AE reaction followed by double AD reaction. Simultaneous two ring closure reactions provided both the THP and THF rings in a single step.
引用
收藏
页码:11279 / 11284
页数:6
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