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Nitroso-ene cyclization enabled access to 1-azaspiro[4.4]nonane and its application in a modular synthesis toward (±)-cephalotaxine
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2015-10-09 , DOI: 10.1016/j.tetlet.2015.10.002 Sha-Hua Huang , Xuechao Tian , Xianwei Mi , Yan Wang , Ran Hong
中文翻译:
亚硝基环化使得能够获得1-azaspiro [4.4]壬烷及其在(±)-头孢他辛模块化合成中的应用
更新日期:2015-10-09
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2015-10-09 , DOI: 10.1016/j.tetlet.2015.10.002 Sha-Hua Huang , Xuechao Tian , Xianwei Mi , Yan Wang , Ran Hong
In this communication, a nitroso-ene cyclization was devised to rapidly construct 1-azaspiro[4.4]nonane, a key structural motif which was further implemented into the modular synthesis of (±)-cephalotaxine (6). The whole synthesis route to access the key intermediate 7 involves eight steps from a commercially available 1,2-epoxycyclopentane (12) and five purifications on silica gel column. The direct nitroso-ene reaction to 1-azabicyclo[4.4]non-2-one paves a way to a future development of the practical synthesis of cephalotaxus alkaloids.
中文翻译:
![](https://scdn.x-mol.com/jcss/images/paperTranslation.png)
亚硝基环化使得能够获得1-azaspiro [4.4]壬烷及其在(±)-头孢他辛模块化合成中的应用
在这种交流中,设计了亚硝基烯环化反应以快速构建1-azaspiro [4.4]壬烷,这是一个关键的结构基序,该基序被进一步实现为(±)-头孢他辛的模块化合成(6)。进入关键中间体7的整个合成路线涉及从市售1,2-环氧环戊烷(12)进行的八个步骤,以及在硅胶柱上进行五个纯化。与1-氮杂双环[4.4]非-2-酮的直接亚硝基反应为将来合成头孢类生物碱的发展铺平了道路。