Total Synthesis and Stereochemical Revision of Iriomoteolide-2a
Total Synthesis and Stereochemical Revision of Iriomoteolide-2a
复制标题
Iriomoteolide-2a的全合成和立体化学修饰
DOI：
10.1002/anie.201800507
复制
发表时间：
2018
期刊：
影响因子：
--
通讯作者：
H.
中科院分区：
文献类型：
--
作者：
Sakamoto;K.; Hakamata;A.; Tsuda;M.; Fuwa;H.
首次完成了iriomoteetreatine-2a的建议和正确结构的全合成，iriomoteetreatine-2a是一种具有不寻常的23元大环内酯骨架的细胞毒性海洋大环内酯天然产物。正确结构的合成涉及用于构建双（四氢呋喃）部分的不对称环氧化/二环氧化物环化级联，用于片段组装的Suzuki-Miyaura偶联，以及用于闭合大环骨架的闭环复分解。此外，修订了iriomotetetra-2a的原始立体化学分配。
Total syntheses of the proposed and correct structures of iriomoteolide‐2a, a cytotoxic marine macrolide natural product with an unusual 23‐membered macrolactone skeleton, have been accomplished for the first time. The synthesis of the correct structure involves an asymmetric epoxidation/diepoxide cyclization cascade for the construction of the bis(tetrahydrofuran) moiety, a Suzuki–Miyaura coupling for the fragment assembly, and a ring‐closing metathesis for the closure of the macrocyclic backbone. In addition, the original stereochemical assignment of iriomoteolide‐2a was revised.