Shiva Raju Kasa, Sabitha Gowravaram
Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
Org Biomol Chem. 2017 Aug 2;15(30):6393-6400. doi: 10.1039/c7ob01438d.
The first stereoselective total synthesis of a cytotoxic brevipolide M, which shares a pyrone framework bearing a tetrahydrofuran moiety and a cinnamate group with the readily available (-)-DET, is described. The key steps involved in the synthesis are the epoxide-opening, Brown's allylation, and the RCM reaction to install an α,β-unsaturated lactone ring and the inversion of the C-6' stereogenic hydroxyl group using the Mitsunobu reaction.
本文描述了细胞毒性短叶内酯M的首次立体选择性全合成，它与易于获得的(-)-DET共享一个带有四氢呋喃部分和肉桂酸酯基团的吡喃酮骨架。合成过程中的关键步骤包括环氧化合物开环、布朗烯丙基化反应、用于构建α,β-不饱和内酯环的RCM反应以及使用 Mitsunobu反应对C-6'立体异构羟基进行构型翻转。
