Lanier Megan L, Park Hyeri, Mukherjee Paramita, Timmerman Jacob C, Ribeiro Anthony A, Widenhoefer Ross A, Hong Jiyong
Department of Chemistry, Duke University, Durham, North Carolina, 27708, USA.
Hammond High Magnet School, 45168 River Rd, Hammond, Louisiana, 70401, USA.
Chemistry. 2017 May 29;23(30):7180-7184. doi: 10.1002/chem.201700499. Epub 2017 May 3.
8-Membered cyclic ethers are found in a wide range of natural products; however, they are challenging synthetic targets due to enthalpic and entropic barriers. The gold(I)-catalyzed intramolecular dehydrative alkoxylation of ω-hydroxy allylic alcohols was explored to stereoselectively construct α,α'-cis-oxocenes and further applied in a formal synthesis of (+)-laurencin. The gold(I)-catalyzed intramolecular dehydrative alkoxylation may constitute an alternative method for the synthesis of molecular building blocks and natural products that contain highly functionalized 8-membered cyclic ethers.
八元环醚存在于多种天然产物中;然而,由于焓垒和熵垒,它们是具有挑战性的合成目标。人们探索了金(I)催化的ω-羟基烯丙醇分子内脱水烷氧基化反应,以立体选择性地构建α,α'-顺式氧杂环辛烷,并进一步应用于(+)-月桂霉素的形式合成。金(I)催化的分子内脱水烷氧基化反应可能为合成含有高度官能团化八元环醚的分子构建单元和天然产物提供一种替代方法。