BioCIS , Univ. Paris-Sud, CNRS, Université Paris-Saclay , 92290 Châtenay-Malabry , France.
Org Lett. 2018 Jun 1;20(11):3192-3196. doi: 10.1021/acs.orglett.8b01020. Epub 2018 May 15.
A new and efficient convergent approach toward the synthesis of amphidinolide F is described through the assembly of three fragments. The two trans-tetrahydrofurans were built by a diastereoselective C-glycosylation with titanium enolate of bulky N-acetyloxazolidinethiones. The side chain was inserted by a Liebeskind-Srogl cross-coupling reaction. A sulfone condensation/desulfonylation sequence, a Stille cross-coupling, and a macrolactonization were applied to connect the fragments.
描述了一种通过三个片段组装合成 Amphidinolide F 的新的有效收敛方法。两个反式四氢呋喃通过钛烯醇盐与大位阻 N-乙酰氧唑烷硫酮的非对映选择性 C-糖苷化反应构建。侧链通过 Liebeskind-Srogl 交叉偶联反应插入。应用亚砜缩合/脱硫反应、Stille 交叉偶联和大环内酯化将片段连接起来。
