State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
Org Lett. 2021 Jun 18;23(12):4532-4537. doi: 10.1021/acs.orglett.1c01157. Epub 2021 Apr 29.
A strategy for the stereoselective synthesis of desacyl furanmonogones A and B has been achieved. The key steps in this synthesis are (1) an Fe(ClO)-mediated oxidative radical cyclization for construction of a -fused [5-6]-bicyclic core with a bridged lactone substitute, (2) a phosphorane-mediated rearrangement to convert the -fused [5-6]-bicyclic core to the corresponding -fused [5-6]-bicyclic core, and (3) a Au-catalyzed cascade reaction for formation of the 4,5--3(2)-furanone motif.
已经实现了去酰基呋喃单加氧酶 A 和 B 的立体选择性合成策略。该合成的关键步骤包括:(1)Fe(ClO)介导的氧化自由基环化反应,构建带有桥连内酯取代基的 -稠合[5-6]-双环核心;(2)膦介导的重排反应,将 -稠合[5-6]-双环核心转化为相应的 -稠合[5-6]-双环核心;(3)Au 催化的级联反应,形成 4,5--3(2)-呋喃酮基序。