Stereo-controlled synthesis of prelasalocid, a key precursor proposed in the biosynthesis of polyether antibiotic lasalocid A
Stereo-controlled synthesis of prelasalocid, a key precursor proposed in the biosynthesis of polyether antibiotic lasalocid A
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DOI：
10.1016/j.tetlet.2007.12.003
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发表时间：
2008-02-04
影响因子：
1.8
通讯作者：
Oikawa, Hideaki
中科院分区：
文献类型：
--
作者：
Migita, Akira;Shichijo, Yoshihiro;Oikawa, Hideaki
在聚醚离子载体抗生素拉沙洛西A的生物合成中，由四氢呋喃连接到四氢吡喃组成的环醚骨架可以通过线性十二酮二烯前体的氧化环化来构建。因此，我们假设具有（E，E）-三取代的烯烃的prelasalocid作为十二酮生物合成前体。一种立体控制的合成路线prelasalocid已被设计在一个高度收敛的方式，需要安装在三取代的烯烃的各种取代基。(c)2007爱思唯尔有限公司保留所有权利。
In the biosynthesis of a polyether ionophore antibiotic, lasalocid A, the cyclic ether skeleton composed of a tetrahydrofuran linked to a tetrahydropyran could be constructed by oxidative cyclization of linear dodecaketide diene precursor. Hence, we hypothesized a prelasalocid having (E,E)-trisubstituted olefins as the dodecaketide biosynthetic precursor. A stereo-controlled synthetic route to the prelasalocid has been devised in a highly convergent manner entailing installation of a variety of substituents at the trisubstituted olefins. (c) 2007 Elsevier Ltd. All rights reserved.