立体选择性烯丙基锡烷加成反应在复杂分子的汇聚合成中的应用。
Stereoselective Allylstannane Addition for a Convergent Synthesis of a Complex Molecule.
机构信息
Institute for Research in Biomedicine, Barcelona Science Park-University of Barcelona , Baldiri Reixac 10, E-08028 Barcelona, Spain.
Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona , 08028 Barcelona, Spain.
出版信息
Org Lett. 2015 Dec 18;17(24):6246-9. doi: 10.1021/acs.orglett.5b03252. Epub 2015 Dec 7.
A convergent methodology with 13 lineal steps for the synthesis of phormidolides B and C macrocyclic core is described. Stereoselective formation of the tetrahydrofuran (THF) core was achieved using a stereocontrolled allylation reaction. The key step of the synthesis is a (Z)-1,5-anti stereoselective allylstannane addition where a new stereocenter and a trisubstituted double bond are formed simultaneously. Finally, Shiina macrolactonization conditions improved the yield of the final cyclization.
描述了一种具有 13 个线性步骤的汇聚方法，用于合成 phormidolide B 和 C 的大环核心。通过立体控制的烯丙基化反应实现了四氢呋喃 (THF) 核心的立体选择性形成。该合成的关键步骤是 (Z)-1,5-anti 立体选择性烯丙基锡烷加成，其中同时形成新的立体中心和三取代双键。最后，Shiina 大环内酯化条件提高了最终环化的产率。
Zotero 插件