Total synthesis of (+)-manzamine A.
Total synthesis of (+)-manzamine A.
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DOI：
10.1021/ja103721s
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发表时间：
2010-07
影响因子：
15
通讯作者：
Tatsuya Toma;Yoichi Kita;T. Fukuyama
中科院分区：
文献类型：
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作者：
Tatsuya Toma;Yoichi Kita;T. Fukuyama
开发了一条合成（+）-曼扎胺A的新路线。它突出了一个非常有效的建设高度紧张的15元环在环己烯酮环的目的是安装在一个完全立体控制的方式所需的功能。其他关键特征包括光学活性丁烯二酸酯的立体选择性Diels-Alder反应，通过对甲苯磺酰酰胺的分子内Mitsunobu反应构建15元环，氰酸烯丙酯的[3，3]-σ-转移重排用于在空间拥挤位置立体选择性引入氮官能度，以及在不稳定官能团存在下的闭环复分解。
A novel synthetic route to (+)-manzamine A was developed. It highlights an amazingly efficient construction of a highly strained 15-membered ring across a cyclohexenone ring with the aim of installing the requisite functionalities in a completely stereocontrolled manner. Other key features include a stereoselective Diels-Alder reaction of an optically active butenolide, construction of the 15-membered ring by intramolecular Mitsunobu reaction of a nosyl amide, [3,3]-sigmatropic rearrangement of allyl cyanate for stereoselective introduction of nitrogen functionality at a sterically congested position, and a ring-closing metathesis in the presence of labile functional groups.