Department of Chemistry and Department of Medicinal Chemistry, Purdue University , 560 Oval Drive, West Lafayette, Indiana 47907, United States.
Org Lett. 2016 May 6;18(9):2296-9. doi: 10.1021/acs.orglett.6b00942. Epub 2016 Apr 26.
An enantioselective total synthesis of (+)-amphirionin-4 has been accomplished in a convergent manner. The synthesis features an efficient enzymatic lipase resolution to access the tetrahydrofuranol core in optically active form. The functionalized tetrahydrofuran derivative was synthesized via an oxocarbenium ion-mediated highly diastereoselective syn-allylation reaction. The polyene side chain was synthesized using Stille coupling reactions. Nozaki-Hiyama-Kishi coupling was utilized to construct the C-8 stereocenter and complete the synthesis of (+)-amphirionin-4.
已以收敛方式完成了 (+)-amphirionin-4 的对映选择性全合成。该合成的特点是采用高效的酶脂肪酶拆分以光学活性形式获得四氢呋喃醇核心。通过氧杂羰鎓离子介导的高度非对映选择性顺式烯丙基化反应合成了官能化的四氢呋喃衍生物。多烯侧链通过 Stille 偶联反应合成。Nozaki-Hiyama-Kishi 偶联用于构建 C-8 立体中心并完成 (+)-amphirionin-4 的合成。