(-)-Enigmazole A 和 (-)-15-O-亚甲基 Enigmazole A 的全合成。
Unified Total Synthesis of (-)-Enigmazole A and (-)-15-O-Methylenigmazole A.
机构信息
Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai, 980-8577, Japan.
Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo, 112-8551, Japan.
出版信息
Chem Asian J. 2020 Nov 2;15(21):3494-3502. doi: 10.1002/asia.202001015. Epub 2020 Oct 1.
The total synthesis of cytotoxic marine phosphomacrolides, (-)-enigmazole A and (-)-15-O-methylenigmazole A, is described in detail. The 2,6-cis-substituted tetrahydropyran ring was efficiently elaborated by using a tandem olefin cross-metathesis/intramolecular oxa-Michael addition reaction. The 18-membered macrolactone skeleton was forged via a Au-catalyzed propargylic benzoate rearrangement/macrocyclic ring-closing metathesis sequence. Late-stage diversification of a common intermediate enabled unified total synthesis of (-)-enigmazole A and (-)-15-O-methylenigmazole A.
详细描述了细胞毒性海洋磷霉素 (-)-enigmazole A 和 (-)-15-O-亚甲氧基 enigmazole A 的全合成。通过串联烯烃交叉复分解/分子内氧杂-Michael 加成反应有效地构建了 2,6-顺式取代的四氢吡喃环。通过 Au 催化的炔丙基苯甲酸酯重排/大环环化复分解序列形成了 18 元大环内酯骨架。通过对一个共同中间体的后期多样化，实现了 (-)-enigmazole A 和 (-)-15-O-亚甲氧基 enigmazole A 的统一全合成。
Zotero 插件