Xue Zhengwen, Li Qingong, Zhang Jingyang, Tang Yefeng
School of Pharmaceutical Sciences, MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Tsinghua University, Beijing 100084, China.
Shandong NHU Pharmaceutical Co., Ltd., No. 01999 Xiangjiang West Second Street, Binhai Economic and Technological Development Zone, Weifang 261108, Shandong Province, China.
Org Lett. 2021 Nov 19;23(22):8783-8788. doi: 10.1021/acs.orglett.1c03280. Epub 2021 Nov 1.
A formal biomimetic synthesis of (+)-hippolachnin A has been achieved under the guidance of its plausible biosynthetic pathway. Pivotal transformations include an intriguing O-mediated [4 + 2] cycloaddition and a tandem Kornblum-DeLaMare rearrangement/hemiketalization/dehydration reaction. The current work not only offers a unified approach to access skeletally diverse plakortin-type polyketides but also provides convincing evidence to elucidate their underlying biosynthetic network.
在合理的生物合成途径指导下，已实现了（+）-海马海绵素A的形式仿生合成。关键转化包括一个有趣的氧介导的[4 + 2]环加成反应以及串联的科恩布卢姆-德拉马尔重排/半缩酮化/脱水反应。当前的工作不仅提供了一种统一的方法来获得骨架多样的 plakortin 型聚酮化合物，还为阐明其潜在的生物合成网络提供了令人信服的证据。
