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Catalytic Hydroxycyclopropanol Ring-Opening Carbonylative Lactonization to Fused Bicyclic Lactones
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-07-20 , DOI: 10.1021/jacs.0c06179 Xinpei Cai 1 , Weida Liang 1 , Mingxin Liu 1 , Xiating Li 1 , Mingji Dai 1
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-07-20 , DOI: 10.1021/jacs.0c06179 Xinpei Cai 1 , Weida Liang 1 , Mingxin Liu 1 , Xiating Li 1 , Mingji Dai 1
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A novel palladium-catalyzed ring opening carbonylative lactonization of readily available hydroxycyclopropanols was developed to efficiently synthesize tetrahydrofuran (THF) or tetrahydropyran (THP)-fused bicyclic γ-lactones, two privileged scaffolds often found in natural products. The reaction features mild reaction conditions, good functional group tolerability, and scalability. Its application was demonstrated in a short total synthesis of (±)-paeonilide. The fused bicyclic γ-lactone products can be easily diversified to other medicinally important scaffolds, which further broadens the application of this new carbonylation method.
中文翻译：
催化羟基环丙醇开环羰基内酯化生成稠合双环内酯
开发了一种新型钯催化的易得羟基环丙醇的开环羰基内酯化反应，以有效合成四氢呋喃（THF）或四氢吡喃（THP）稠合双环γ-内酯，这是天然产物中常见的两种特殊支架。该反应具有反应条件温和、官能团耐受性好、可扩展等特点。它的应用在(±)-芍药内酯的简短全合成中得到了证明。稠合双环γ-内酯产品可以很容易地多样化为其他医学上重要的支架，这进一步拓宽了这种新的羰基化方法的应用。
更新日期：2020-07-20
中文翻译：
催化羟基环丙醇开环羰基内酯化生成稠合双环内酯
开发了一种新型钯催化的易得羟基环丙醇的开环羰基内酯化反应，以有效合成四氢呋喃（THF）或四氢吡喃（THP）稠合双环γ-内酯，这是天然产物中常见的两种特殊支架。该反应具有反应条件温和、官能团耐受性好、可扩展等特点。它的应用在(±)-芍药内酯的简短全合成中得到了证明。稠合双环γ-内酯产品可以很容易地多样化为其他医学上重要的支架，这进一步拓宽了这种新的羰基化方法的应用。
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