Total Synthesis of (－)‐Enigmazole A
Total Synthesis of (－)‐Enigmazole A
复制标题
(－)-恩尼格唑A的全合成
DOI：
10.1002/anie.201801561
复制
发表时间：
2018
期刊：
影响因子：
--
通讯作者：
H. Fuwa
中科院分区：
文献类型：
--
作者：
K. Sakurai;M. Sasaki;H. Fuwa
完成了具有细胞毒活性的海洋大环内酯类天然产物（−）-enigmazole A的全合成。四氢吡喃部分通过δ-羟基烯烃的多米诺烯烃交叉复分解/分子内氧杂-迈克尔加成来构建。在高级中间体偶联后，通过苯甲酸炔丙酯的金催化重排，然后通过所得α，β-不饱和酮的闭环复分解形成大环。
Total synthesis of (−)‐enigmazole A, a marine macrolide natural product with cytotoxic activity, has been accomplished. The tetrahydropyran moiety was constructed by means of a domino olefin cross‐metathesis/intramolecular oxa‐Michael addition of a δ‐hydroxy olefin. After coupling of advanced intermediates, the macrocycle was formed through gold‐catalyzed rearrangement of a propargylic benzoate, followed by ring‐closing metathesis of the resultant α,β‐unsaturated ketone.