Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor
Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor
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DOI：
10.1021/ja0276826
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发表时间：
2002-10-16
影响因子：
15
通讯作者：
Osada, H
中科院分区：
文献类型：
--
作者：
Hayashi, Y;Shoji, M;Osada, H
血管生成抑制剂(−)-氮阿司匹林的不对称全合成已经完成，建立了它的绝对立体化学。关键步骤是由溴化镁介导的非对映选择性的Mukaiyama Aldol反应，NaH促进的炔胺的分子内环化反应，以及含有官能化的γ-内酰胺部分的酮的Aldol反应而不保护叔醇和酰胺官能团。
The asymmetric total synthesis of (−)-azaspirene, an angiogenesis inhibitor, has been accomplished, establishing its absolute stereochemistry. The key steps are a MgBr2·OEt2-mediated, diastereoselective Mukaiyama aldol reaction, a NaH-promoted, intramolecular cyclization of an alkynylamide, and the aldol reaction of a ketone containing functionalized γ-lactam moiety without protection oftert-alcohol and amide functionalities.