Total Synthesis of (−)-Luminacin D

A second-generation synthesis of (−)-luminacin D based on an early stage introduction of the trisubstituted epoxide group is reported, allowing access to the natural product in an improved yield and a reduced number of steps (5.4%, 17 steps vs 2.6%, 19 steps). A full account of the optimization work is provided, with the reversal of stereoselection in the formation of the C4 alcohol in equally excellent diastereoselectivity as the key improvement.本研究报道了基于三取代环氧基团早期引入策略的(-)-亮菌素D（(-)-luminacin D）第二代全合成路线。该路线可提升目标天然产物的合成产率并精简反应步骤：总产率达5.4%，共17步，相较原路线的2.6%产率与19步反应具有显著优势。本研究详细记述了整条合成路线的优化过程，其中核心改进为反转了C4位醇形成过程中的立体选择性，且该步骤仍可保持同等优异的非对映选择性。