Department of Chemistry , Massachusetts Institute of Technology , Cambridge , Massachusetts 02139 , United States.
J Am Chem Soc. 2019 Jul 17;141(28):11239-11244. doi: 10.1021/jacs.9b04696. Epub 2019 Jul 8.
Herein, we report the first total synthesis of marine ladder polyether gymnocin B () based on a two-phase strategy. In Phase I, inspired by the proposed biosynthesis, epoxide-opening cascades assemble 10 out of 15 cyclic ether rings making up the molecular core. In the subsequent Phase II, coalescence elevates the molecular complexity further by coupling of these subunits. Our two-phase synthetic approach significantly improved the step efficiency of the synthesis of this class of natural products.
本文报道了基于两相策略的海洋 ladder polyether gymnocin B()的首次全合成。在第一相中,受提出的生物合成启发,环氧开环级联反应组装了构成分子核心的 15 个环醚环中的 10 个。在随后的第二相中,这些亚基的偶联进一步提高了分子的复杂性。我们的两相合成方法显著提高了这类天然产物合成的步骤效率。